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

HRID 1706020Notes

Reaction equation

HRID 1706020 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-0d792513da1b43729aa942c579e47b56
Source dataset
uspto-grants-1980_06
Patent number
US04206121

Reaction notes

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