Chlorotrimethylsilane → Ethyl [(trimethylsilyl)sulfanyl]acetate

HRID 742781Notes

Reaction equation

HRID 742781 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. 1HNMR (300 MHz, CDCl3) δ4.18 (2H, q, J=7.19 Hz), 3.20 (2H, s), 1.29 (3H, t, J=7.12 Hz), 0.35 (9H, s).

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-5c0bf23d63e84202ae54e13d45874d25
Source dataset
uspto-grants-1996_09
Patent number
US05554767

Reaction notes

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