2,2-dimethylindene-1,3-dione

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 2,2-dimethyl-indan-1,3-dione (430 mg, 2.47 mmol), which can be prepared as described in Example 18, in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one hour the reaction is quenched with saturated aqueous NH4Cl and the mixture is brought to room temperature. The reaction mixture is concentrated to approximately half of its original volume and then diluted with ethyl acetate and washed with water. The aqueous layer is then back-extracted two times with ethyl acetate. The organic layers are combined, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6) to afford 3-hydroxy-2,2-dimethyl-indan-1-one; MS: (ESI) m/z 177.0 (M+H)+. After one hour the reaction is quenched with saturated aqueous NH4Cl is brought to room temperature The reaction mixture is concentrated to approximately half of its original volume diluted with ethyl acetate washed with water The aqueous layer is then back-extracted two times with ethyl acetate dried with Na2SO4 filtered concentrated The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6)

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

実験手順: Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (5.8 g, ˜50 mmol) is heated at 135° C. for 2 hours under vacuum (<20 torr). The solid is then permitted to cool to room temperature and placed under a nitrogen atmosphere at which time a solution of indan-1,3-dione (CAS#606-23-5, 1.46 g, 10.0 mmol) in acetonitrile (15 mL) is added followed by iodomethane (1.8 mL, 30 mmol). The reaction is heated in a sealed vessel at 70° C. overnight. The reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The eluent is concentrated and the resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 2,2-dimethyl-indan-1,3-dione 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 6 H), 7.84-7.89 (m, 2 H), 7.96-8.02 (m, 2 H). is added The reaction is heated in a sealed vessel at 70° C. overnight The reaction mixture is cooled to room temperature filtered through a pad of Celite® The eluent is concentrated the resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9)

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

実験手順: To a solution of 2,2-dimethyl-indan-1,3-dione (430 mg, 2.47 mmol), in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one h the reaction is quenched with saturated aqueous NH4Cl and the mixture is brought to room temperature. The reaction mixture is concentrated to approximately half of its original volume and then diluted with ethyl acetate and washed with water. The aqueous layer is then back-extracted twice with ethyl acetate. The organic layers are combined, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6) to afford 3-hydroxy-2,2-dimethyl-indan-1-one; MS (ESI) m/z 177.0 (M+H)+. After one h the reaction is quenched with saturated aqueous NH4Cl is brought to room temperature The reaction mixture is concentrated to approximately half of its original volume diluted with ethyl acetate washed with water The aqueous layer is then back-extracted twice with ethyl acetate dried with Na2SO4 filtered concentrated The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6)

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

実験手順: Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (5.8 g, ˜50 mmol) is heated at 135° C. for 2 h under vacuum (<20 torr). The solid is then permitted to cool to room temperature and placed under a nitrogen atmosphere at which time a solution of indan-1,3-dione (CAS# 606-23-5, 1.46 g, 10.0 mmol) in acetonitrile (15 mL) is added followed by iodomethane (1.8 mL, 30 mmol). The reaction is heated in a sealed vessel at 70° C. overnight. The reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 2,2-dimethyl-indan-1,3-dione; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (s, 6 H), 7.84-7.89 (m, 2 H), 7.96-8.02 (m, 2 H). is added The reaction is heated in a sealed vessel at 70° C. overnight The reaction mixture is cooled to room temperature filtered through a pad of Celite® The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9)

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Preparations of compounds listed in the above Table I are given below for illustrative purposes. ##STR76## 20 g (0.137 moles) of indan-1,3-dione was added to 200 ml of acetonitrile. 26 ml (0.41 moles) of methyl iodide and 8 g of a KF-celite (1:1) mixture were then added to this mixture and the resulting red mixture stirred for 18 hours at 60° C. under a nitrogen atmosphere. After cooling, the precipitate was filtered off and washed with acetonitrile. The filtrate was then evaporated to dryness and the residue chromatographically purified using a silica column with hexane/ether (6:4) as the eluent. 10.5 g of 2,2-dimethyl-indan-1,3-dione was obtained with a melting point of 107° C. ##STR77## After cooling the precipitate was filtered off washed with acetonitrile The filtrate was then evaporated to dryness the residue chromatographically purified