Benzyl mercaptan → alpha-Benzylthiomethyl-beta-(p-chlorophenyl)-gamma-butyrolactone

HRID 65265Notes

Reaction equation

HRID 65265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][O:12][C:10](=[O:11])[C:9]2=[CH2:14])=[CH:4][CH:3]=1.[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C.C(OCC)C>[CH2:15]([S:22][CH2:14][CH:9]1[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:13][O:12][C:10]1=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 7509Benzyl mercaptanHCID 20234200beta-(p-Chlorophenyl)-alpha-methylene-gamma-butyrolactone

Product 1

HCID 13518985alpha-Benzylthiomethyl-beta-(p-chlorophenyl)-gamma-butyrolactoneYield 81%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 700 mg of β-(p-chlorophenyl)-α-methylene-γ-butyrolactone in 10 ml of toluene were added 0.51 ml of benzylmercaptan and one drop of triethylamine and the resulting mixture was kept at room temperature for 6 hours. After completion of the reaction, the reaction mixture was diluted with 100 ml of ethyl ether, washed with 10% aqueous sodium hydroxide and saturated saline, dried over magnesium sulfate and the solvent was distilled off. The crude product thus obtained was purified by a column chromatography to give 900 mg (yield 81%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washwashed with 10% aqueous sodium hydroxide and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe crude product thus obtained
  6. customwas purified by a column chromatography

Sources & evidence

ORD record
ord-e3ebcc3beb1645798651b66d77616bf4
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Reaction notes

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