Methanol → Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

反応式

[CH3:1][C:2]1(C)[CH2:9][CH:8]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:7][CH2:6][O:5][C:3]1=O.[CH3:23][O-:24].[Na+].[CH3:26][OH:27]>>[CH3:1][C:2]([CH3:3])([CH2:9][CH:8]([CH2:7][CH2:6][OH:5])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])[C:23]([O:27][CH3:26])=[O:24]

参加物

反応物 3

HCID 887Methanol

HCID 99966312,2-Dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactone

HCID 10942334Sodium Methoxide

生成物 1

HCID 14986673Methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsiloxy)octanoate

実験手順

To a solution of 2.35 g (7.2 mmol) of 2,2-dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactone in 22 ml methanol is added 0.386 g (7.2 mmol) sodium methoxide and the mixture is stirred for 2.5 h. The reaction is quenched with saturated aqueous ammonium chloride and extracted twice with methylene chloride. The combined organic extracts are washed with water and brine, dried, filtered and evaporated to yield methyl 2,2-dimethyl-4-(2-hydroxyethyl)-8-(t-butyldimethylsilyloxy)-octanoate as an oil; NMR (CDCl3): delta 3.67 (s,3H), 3.55-3.65 (m,4H), 1.18 (s,6H), 0.89 (s,9H).