Sodium benzenethiolate → Methyl 4-oxo-5-(phenylsulfanyl)pentanoate

HRID 463508

Reaction equation

HRID 463508 reaction equation
[C:1]1([S-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[CH3:9][O:10][C:11](=[O:18])[CH2:12][CH2:13][C:14](=[O:17])[CH2:15]Br>>[CH3:9][O:10][C:11](=[O:18])[CH2:12][CH2:13][C:14](=[O:17])[CH2:15][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 9855825Methyl 5-bromo-4-oxopentanoate

Product 1

HCID 13709046Methyl 4-oxo-5-(phenylsulfanyl)pentanoate

Procedure

To 100 ml of a 1M methanolic sodium thiophenolate solution there was added 22 g (0.1 mole) 5-bromo-4-oxo-valeric acid methylester during 40 minutes and the reaction mixture was stirred for two hours at room temperature. The methanol was distilled off in vacuo, to the residue there was added 200 ml ethyl acetate, and the mixture was washed successively with 30 water, 30 ml sodium bicarbonate solution, 30 ml saturated saline solution, then dried over magnesium sulfate, filtered, and the solvent was distilled off. The residue was chromatographed on a column using a 4:1 mixture of hexane and ethyl acetate as an eluent.

Workup

  1. distillationThe methanol was distilled off in vacuo, to the residue there
  2. additionwas added 200 ml ethyl acetate
  3. washthe mixture was washed successively with 30 water, 30 ml sodium bicarbonate solution, 30 ml saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off
  7. customThe residue was chromatographed on a column
  8. additiona 4:1 mixture of hexane and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-55ede65e228e4d70bd80b46e05aa2aae
Source dataset
uspto-grants-1985_05
Patent number
US04520018

Linked notes

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