beta-(p-Chlorophenyl)-alpha-methylene-gamma-butyrolactone → S-[[4-(4-chlorophenyl)-2-oxooxolan-3-yl]methyl] benzenecarbothioate

HRID 65261Notes

Reaction equation

HRID 65261 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.[C:15]([OH:23])(=[S: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>[C: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])(=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 20234200beta-(p-Chlorophenyl)-alpha-methylene-gamma-butyrolactoneHCID 178526132HCID 178526132, compound

Product 1

HCID 13715528S-[[4-(4-chlorophenyl)-2-oxooxolan-3-yl]methyl] benzenecarbothioateYield 75%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 600 mg of β-(p-chlorophenyl)-α-methylene-γ-butyrolactone in 10 ml of toluene were added 0.44 ml of thiobenzoic acid and one drop of triethylamine and the reaction was effected at room temperature for 18 hours. The reaction mixture was diluted with 100 ml of ethyl ether, washed with water and saturated saline, dried over magnesium sulfate and the solvent was then distilled off. The crude product thus obtained was purified by a silica gel column chromatography to give 750 mg (yield 75%) of the title compound.

Workup

  1. washwashed with water and saturated saline
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. customThe crude product thus obtained
  5. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-3b7073b3151c4a99bac17ba77a9f95d0
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Reaction notes

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