Diethyl Ether → Methyl 4-{[tert-butyl(dimethyl)silyl]oxy}butanoate

HRID 878622Notes

Reaction equation

HRID 878622 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:15]COCC>>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 1868234-{[tert-Butyl(dimethyl)silyl]oxy}butanoic acid

Product 1

HCID 15399104Methyl 4-{[tert-butyl(dimethyl)silyl]oxy}butanoateYield 95%

Procedure

CH2N2 (1.04 g, 248.1 mmol) in ether (10 mL) was added to 4-[tert-butyl(dimethyl)silyl]oxybutanoic acid (5.41 g, 24.81 mmol) in a flask. The mixture was stirred overnight, concentrated to give the title compound (5.44 g, 95%). 1H NMR (400 MHz, CDCl3): δ 0.03 (6H, s), 0.88 (9H, s), 1.81-184 (2H, m), 2.39 (2H, t, J=7.2 Hz), 3.63 (2H, d, J=6.4 Hz), 3.66 (3H, s). [M+H] Calc'd for C11H24O3Si, 233; Found, 233.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f9f7c76087a24fda879b5e578281cccf
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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