4-hydroxybutyl prop-2-enoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of probucol (2.58 g, 5 mmol) in THF (50 ML) were added 4-hydroxybutyl acrylate (1.0 ml, 10 mmol), triphenylphosphine (2.62 g, 10 mmol) and diethyl azodicarboxylate (1.57 ml, 10 mmol). The resultant mixture was stirred under nitrogen at reflux over weekend. It was evaporated. Silica gel chromatography (hexanes/dichloromethane 4:1) gave the title compound as a brown oil (0.92 g). 1H-NMR (400 MHz, CDCl3): 7.54 (s, 2 H), 7.46 (s, 2 H), 6.42 (dd, 1 H), 6.14 (dd, 1 H), 5.84 (dd, 1 H), 5.38 (s, 1 H), 4.23 (t, 2 H), 3.75 (t, 2 H), 1.97 (m, 2 H), 1.82 (m, 2 H), 1.46 (s, 6 H), 1.45 (s, 18 H), 1.42 (s, 18 H). at reflux over weekend It was evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Propyl-cyclohexanecarboxylic acid (10.0 g, 58.0 mmol), 4-hydroxybutyl acrylate (8.0 g, 57.0 mmol) and a catalytic amount of para-toluene sulphonic acid are stirred under reflux in toluene (100 ml) in a flask equipped with Dean-Stark apparatus. The reaction is shown to be complete by GCMS after 1 hour. The solution is allowed to cool to room temperature, is washed with aqueous sodium carbonate and water, dried and evaporated to dryness. Purification is achieved by flash column chromatography using petrol as eluant. Evaporation of the appropriate fractions gives a colourless oil. equipped with Dean-Stark apparatus is washed with aqueous sodium carbonate and water dried evaporated to dryness Purification Evaporation of the appropriate fractions gives a colourless oil

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of 1-chloroethyl chloroformate (1.20 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 2.26 g (90%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.80 (4 H, m, CH2 --CH2), 1.86 (3 H, d, J=5 Hz, CH3), 4.24 (4 H, m, 2×CH2 --O), 5.7-6.6 (4 H, m, CH=CH2 and CH). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml) The organic phase is dried (MgSO4) the solvent evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of 1-chloroethyl chloroformate (1.20 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 2.26 g (90%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.80 (4 H, m, CH2 --CH2), 1.86 (3 H, d, J=5 Hz, CH3), 4.24 (4 H, m, 2×CH2 --O), 5.7-6.6 (4 H, m, CH=CH2 and CH). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml) The organic phase is dried (MgSO4) the solvent evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of chloromethyl chloroformate (0.98 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4 H, m, CH2 --CH2), 4.27 (4 H, m, 2×CH2 --O), 5.77 (2 H, s, Cl--CH2 --O), 5.8-6.7 (3 H, m, CH=CH2). The reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml) The organic phase is dried (MgSO4) the solvent evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of chloromethyl chloroformate (0.98 ml, 11.00 mmol) and 4-hydroxybutyl acrylate (1.38 ml, 10.00 mmol) in dichloromethane (12 ml) at 3° C. under a dry N2 atmosphere. After 15 min. at 3° C. and 17 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure to give 1.76 g (74%) of the title product. 1H NMR (60 MHz, CDCl3): δ 1.82 (4 H, m, CH2 --CH2), 4.27 (4 H, m, 2×CH2 --O), 5.77 (2 H, s, Cl--CH2 --O), 5.8-6.7 (3 H, m, CH=CH2). The reaction mixture is washed with hydrochloric acid (1.00 M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (2×10 ml) The organic phase is dried (MgSO4) the solvent evaporated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound (A) can also be prepared by polymerization of the reaction product of the compound [5] with an α,β-unsaturated hydroxyl compound, such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, dipentaerythritol hexa(meth)acrylate, hexa(meth)acrylate of a compound formed by addition of dipentaerythritol with ε-caprolactone and the like, or with a corresponding α,β-unsaturated thiol compound. The compound (A) can also be prepared by copolymerization of the reaction product with an α,β-unsaturated compound having no functional groups. Examples of the α,β-unsaturated compound having no functional groups are: methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, styrene, α-methylstyrene, p-vinyltoluene, acrylonitrile and the like.

反応条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 500 ml round-bottom flask was placed 0.3 mole of 2-(toluene-4-sulfonyloxy)ethyl acrylate, 0.3 mole of 4-hydroxybutyl acrylate, 0.3 mole of methyl methacrylate, 300 g of tetrahydrofuran (THF), and 0.1 g-3 g of AIBN. The reaction mixture was heated at 60-75° C. for 5-20 hours. The product was precipitated in ethyl ether or n-hexane, filtered and dried to provide poly [2-(toluene-4-sulfonyloxy)ethyl acrylate/4-hydroxybutyl acrylate/-methyl methacrylate] represented by the following chemical formula 19, at a yield of 65-70%. In a 500 ml round-bottom flask was placed The product was precipitated in ethyl ether n-hexane, filtered dried

反応条件: temp:67.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 500 ml round-bottom flask was placed 0.3 mole of 2-(toluene-4-sulfonyloxy)ethyl acrylate, 0.3 mole of 4-hydroxybutyl acrylate, 0.3 mole of methyl methacrylate, 300 g of tetrahydrofuran (THF), and 0.1 g-3 g of AIBN. The reaction mixture was heated at 60-75° C. for 5-20 hours. The product was precipitated in ethyl ether or n-hexane, filtered and dried to provide poly [2-(toluene-4-sulfonyloxy)ethyl acrylate/4-hydroxybutyl acrylate/-methyl methacrylate] represented by the following chemical formula 19, at a yield of 65-70%. In a 500 ml round-bottom flask was placed The product was precipitated in ethyl ether n-hexane, filtered dried