Chlorotrimethylsilane → 2,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester

HRID 1046442Notes

Reaction equation

HRID 1046442 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[CH3:6][O:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][OH:11].C(N(CC)CC)C>ClCCl.C(OCC)C>[CH3:6][O:7][C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][O:11][Si:2]([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 866501662,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

TMSCl (2.30 mL, 0.018 mol) was added dropwise to a solution of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (2.0 g, 0.015 mot) and triethylamine (3.16 mL, 0.023 mol) in dichloromethane at 0° C. After stirring for 1 h, the reaction was warmed to room temperature and stirred for an additional 1.5 h. Volatiles were removed under reduced pressure to provide a solid that was slurried in a mixture of ethyl ether and hexanes. The solid was removed by filtration and the filtrate was concentrated to provide a yellow liquid that was purified by bulb to bulb distillation under reduced pressure to provide 2,2-dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester (2.8 g, 91%) as a colorless liquid.

Workup

  1. stirringstirred for an additional 1.5 h
  2. customVolatiles were removed under reduced pressure
  3. customto provide a solid
  4. customThe solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customto provide a yellow liquid that
  7. distillationwas purified by bulb to bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-ea7eb345fa5b4e99af362e2e861042aa
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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