2-Bromoethanol → methyl 3-(2-hydroxyethylsulfanyl)propanoate

HRID 326101Notes

Reaction equation

HRID 326101 reaction equation
[Na].[SH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH2:10][CH2:11][OH:12]>CO>[OH:12][CH2:11][CH2:10][S:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 18050Methyl 3-mercaptopropionateHCID 5360545Sodium

Product 1

HCID 220049methyl 3-(2-hydroxyethylsulfanyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.3 g. sodium in 80 ml. methanol, which contains 12 g. methyl 3-mercaptopropionate and 12.5 g. 2-bromoethanol, is stirred under reflux for 4 hours. After evaporating, the residue is taken up in chloroform, filtered and evaporated. 16 g. Methyl 3-(2-hydroxyethylthio)-propionate are obtained in the form of an oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter evaporating
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6d2fd456924a463a92178ad5673e9e42
Source dataset
uspto-grants-1984_04
Patent number
US04444766

Reaction notes

Loading…