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

Reaktionsgleichung

[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]

Komponenten

Edukt 3

HCID 887Methanol

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

HCID 10942334Sodium Methoxide

Produkt 1

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

Versuchsvorschrift

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).