HCID 13189248、化合物 → 4-(1-Ethoxyethoxy)-3,3-difluoro-4-methylpentan-1-OL
反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][C:13]([F:24])([F:23])[C:14]([O:17][CH:18]([O:20][CH2:21][CH3:22])[CH3:19])([CH3:16])[CH3:15])(=O)C>CCOCC>[CH2:21]([O:20][CH:18]([O:17][C:14]([CH3:16])([CH3:15])[C:13]([F:23])([F:24])[CH2:12][CH2:11][OH:10])[CH3:19])[CH3:22]参加物
4
反応条件
- 温度
- 35 °C
実験手順
To a mixture of 2.25 g (0.059 mol) of lithium aluminum hydride in 50 mL of ether at 0° C. was added dropwise, 11.30 g (0.040 mol) of 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol 1-acetate in 130 mL of ether. The mixture was heated at reflux (35° C.) for 3 hr and then was recooled to 0° C. The mixture was quenched by adding dropwise 4.5 mL of water followed by 3.6 mL of 10% aqueous sodium hydroxide. The mixture was stirred at 25° C. for 0.5 hr and was filtered. Evaporation of solvent and column chromatography of the residue on 0.06-0.20 mm silica gel afforded 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol. NMR (CDCl3) δ5.00 (quartet, 1, J=7 Hz), 3.86 (broad, 2), 3.51 (quartet, 2, J=7 Hz), 2.25 (multiplet, 2), 1.35 (triplet, 6, J=1 Hz), 1.30 (doublet, 3, J=7 Hz), and 1.18 ppm (triplet, 3, J=7 Hz).