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

HRID 871469Notes

Reaction equation

HRID 871469 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-3c03c9dd34fc430aa8b2ec3509051d8f
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

Loading…