Methanethiol → Ethyl 2-[(methylsulfanyl)methyl]prop-2-enoate

HRID 1447761Notes

Reaction equation

HRID 1447761 reaction equation
[CH3:1][SH:2].[Na].[CH2:4]([O:6][C:7](=[O:12])[C:8]([CH2:10]Br)=[CH2:9])[CH3:5]>C(O)C.O>[CH2:4]([O:6][C:7](=[O:12])[C:8]([CH2:10][S:2][CH3:1])=[CH2:9])[CH3:5]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 5360545Sodium

Product 1

HCID 12463627Ethyl 2-[(methylsulfanyl)methyl]prop-2-enoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of methylmercaptan (4.8 g.) and sodium (2.3 g.) in absolute ethanol (75 ml.) is added dropwise to a solution of ethyl-2-bromomethylacrylate (19.3 g.) in ethanol (25 ml.). After two hours, it is diluted with water (400 ml.) and extracted with methylene chloride. The organic layer is dried and concentrated to dryness in vacuo to yield ethyl-2-methylthiomethylacrylate.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic layer is dried
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-002d8c3eddb240bfab5efcf740eba70a
Source dataset
uspto-grants-1979_12
Patent number
US04178291

Reaction notes

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