tert-Butyldimethylsilyl chloride → Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate

HRID 1038312Notes

Reaction equation

HRID 1038312 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)C(C)C)(C)C.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 12044793Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-hydroxy-2,2-dimethylpropanoate (5.00 g, 38 mmol), N,N-diisopropylethylamine (7.30 g, 57 mmol) and tert-butyldimethylchlorosilane (6.80 g, 45 mmol) in dry DMF (70 mL) was stirred at room temperature for 12 h. The reaction solution was quenched with water (225 mL) and extracted with diethyl ether (3×50 mL). The combined organic extracts were washed with water (100 mL), brine (100 mL), then dried over MgSO4. Concentration under reduced pressure afforded methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate as colorless oil (9.36 g, 100%). It was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 3.64 (s, 3H), 3.55 (s, 2H), 1.13 (s, 6H), 0.85 (s, 9H), 0.0 (s, 6H).

Workup

  1. customThe reaction solution was quenched with water (225 mL)
  2. extractionextracted with diethyl ether (3×50 mL)
  3. washThe combined organic extracts were washed with water (100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-5423a26612bf4de6bab67663bfc1bd57
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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