Ethanethiol → (R)-3-(Ethylthio)-2-hydroxypropanoic acid

HRID 2226577Notes

Reaction equation

HRID 2226577 reaction equation
[Na].Br[C@H:3]([CH2:7]O)[C:4]([OH:6])=[O:5].[CH2:9]([SH:11])[CH3:10].[O-:12]CC.[Na+].C(O)C>C(O)C>[CH2:9]([S:11][CH2:7][C@H:3]([OH:12])[C:4]([OH:6])=[O:5])[CH3:10]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 5360545SodiumHCID 13776211110994-91-7HCID 23706232Ethanol sodium ethoxide

Product 1

HCID 54163107(R)-3-(Ethylthio)-2-hydroxypropanoic acidYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.57 g, 25 mmol) in ethanol (25 ml) was added dropwise to a stirred solution of (R)-2-bromo-3-hydroxypropanoic acid (2.11 g, 12.5 mmol) under nitrogen at -30°. After 30 min the mixture was allowed to warm to room temperature and stirred for a further 1 h. A solution of ethanethiol (1.85 ml, 25 mmol) in sodium ethoxide/ethanol (0.57 g, 25 mmol of sodium in 25 ml ethanol) was added and the mixture stirred overnight. The ethanol was evaporated and the residue dissolved in water. The solution was acidified with hydrochloric acid and extracted with ethyl acetate, the organic extracts were dried (MgSO4) and the solvent evaporated. Chromatography on silica with toluene/acetic acid as eluant gave the sub-title acid (0.79 g).

Workup

  1. stirringthe mixture stirred overnight
  2. customThe ethanol was evaporated
  3. dissolutionthe residue dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic extracts were dried (MgSO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-a26d2cf6fe544216a22d45a80faef001
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

Loading…