3-methoxy-3-methylbutan-1-ol

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:

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

実験手順: Prepared as in Example 215c from 3-methoxy-3-methylbutan-1-ol and 2,6-dinitrobenzonitrile in 52% yield. MS 265 (MH+).

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

実験手順: Prepared as in Example 215c from 3-methoxy-3-methylbutan-1-ol and 2,6-dinitrobenzonitrile in 52% yield. MS 265 (MH+).

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

実験手順: Dess-Martin reagent (15.0 g) was added to a chloroform solution (35 ml) of 3-methoxy-3-methyl-1-butanol (3.3 g) under ice cooling and stirred at room temperature for 5 hours. Chloroform was added to the reaction mixture and the organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure, thereby obtaining a crude product containing 3-methoxy-3-methylbutanal. Hydroxyamine hydrochloride (3.5 g) was added to a pyridine solution of the obtained crude product (30 ml) under ice cooling and stirred at room temperature overnight under nitrogen atmosphere. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%), thereby obtaining (N-hydroxy-3-methoxy-3-methylbutan-1-imine (1.4 g) as a colorless oily substance. the organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate The organic layer was dried over magnesium sulfate the solvent was distilled off under reduced pressure obtaining a crude product obtained crude product (30 ml) under ice cooling stirred at room temperature overnight under nitrogen atmosphere the organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine The organic layer was dried over magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%)

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

実験手順: Prepared as in Example 215c from 3-methoxy-3-methylbutan-1-ol and 2,6-dinitrobenzonitrile in 52% yield. MS 265 (MH+).

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

実験手順: Prepared as in Example 215c from 3-methoxy-3-methylbutan-1-ol and 2,6-dinitrobenzonitrile in 52% yield. MS 265 (MH+).

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: A solution of 3-methoxy-3-methylbutan-1-ol (2.50 g, 21.16 mmol) in DCM (30 mL) was treated with p-toluene sulfonyl chloride (5.00 g, 26.2 mmol) followed by TEA (4.28 g, 42.3 mmol) and stirred at RT for 3 h. The mixture was washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (2.84 g, 49%). 1H NMR (400 MHz, DMSO-d6): δ 7.76 (d, J=8.2 Hz, 2 H), 7.45 (d, J=8.1 Hz, 2 H), 4.03 (t, J=7.2 Hz, 2 H), 2.96 (s, 3 H), 2.38 (s, 3 H), 1.75 (t, J=7.2 Hz, 2 H), 1.01 (s, 6 H); MS (ESI) m/z: 295.0 (M+Na+). The mixture was washed with satd NaHCO3, then brine, dried over Na2SO4 concentrated to dryness

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

実験手順: A solution of 3-methoxy-3-methylbutan-1-ol (2.50 g, 21.16 mmol) in DCM (30 mL) was treated with p-toluene sulfonyl chloride (5.00 g, 26.2 mmol) followed by TEA (4.28 g, 42.3 mmol) and stirred at RT for 3 h. The mixture was washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (2.84 g, 49%). 1H NMR (400 MHz, DMSO-d6): δ 7.76 (d, J=8.2 Hz, 2 H), 7.45 (d, J=8.1 Hz, 2 H), 4.03 (t, J=7.2 Hz, 2 H), 2.96 (s, 3 H), 2.38 (s, 3 H), 1.75 (t, J=7.2 Hz, 2 H), 1.01 (s, 6 H); MS (ESI) m/z: 295.0 (M+Na+). The mixture was washed with satd NaHCO3, then brine, dried over Na2SO4 concentrated to dryness