Methyl Acrylate → Methyl 3-[(2-thienylmethyl)thio]propanoate

HRID 1975676Notes

Reaction equation

HRID 1975676 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][SH:7].[CH3:8][O:9][C:10](=[O:13])[CH:11]=[CH2:12].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][CH2:12][CH2:11][C:10]([O:9][CH3:8])=[O:13]

Participants

5

Reactant 4

HCID 7294Methyl AcrylateHCID 8082PiperidineHCID 66854Benzyltrimethylammonium hydroxideHCID 80408Thenyl mercaptan

Product 1

HCID 15225387Methyl 3-[(2-thienylmethyl)thio]propanoate

Procedure

A solution of 2-thiophenemethanethiol (12 grams), methylacrylate (7.94 grams), piperidine (3 mL) and N-benzyltrimethylammonium hydroxide (3 mi) was stirred for 16 hours at room temperature. The reaction mixture was distilled in vacuo to yield the desired title compound. Yield: 16.5 grams (83%). Bp: 140° C. at 1 mmHg.

Workup

  1. distillationThe reaction mixture was distilled in vacuo

Sources & evidence

ORD record
ord-685c1040e81a482d81ccdd6d5fc0711d
Source dataset
uspto-grants-1994_02
Patent number
US05288719

Reaction notes

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