Chlorotrimethylsilane → Ethyl [(trimethylsilyl)sulfanyl]acetate

HRID 962628Notes

Reaction equation

HRID 962628 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][Si:9](Cl)([CH3:11])[CH3:10].C(N(CC)CC)C>CCOCC>[CH3:8][Si:9]([CH3:11])([CH3:10])[S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 12185Ethyl Thioglycolate

Product 1

HCID 13310493Ethyl [(trimethylsilyl)sulfanyl]acetateYield 68.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl mercaptoacetate (9.0 mL, 83.2 mmol) in 15 mL of anhydrous ether under nitrogen atmosphere was added trimethylsilyl chloride (12.0 mL, 94.6 mmol) followed by triethyl amine (13.0 mL, 93.3 mmol) slowly. White precipitates were formed upon addition of triethyl amine. The suspension was allowed to stir at room temperature overnight. The white precipitate was removed by filtration. The filtrate was concentrated on a rotavap. The residue oil was distilled at 40° C. (0.5 mm Hg) to give 10.9 g (68%) of ethyl (trimethylsilylthio)acetate as a colorless oil.

Workup

  1. customWhite precipitates
  2. customwere formed upon addition of triethyl amine
  3. customThe white precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated on a rotavap
  5. distillationThe residue oil was distilled at 40° C. (0.5 mm Hg)

Sources & evidence

ORD record
ord-f50ae4673ee942fa9aacbe9f8a11eda1
Source dataset
uspto-grants-1998_06
Patent number
US05760048

Reaction notes

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