Acetone → Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioate

HRID 1937337Notes

Reaction equation

HRID 1937337 reaction equation
[CH2:1]=[C:2]([CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH2:25]([SH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)=[O:35]>CN(C)C1C=CN=CC=1>[CH2:25]([S:32]([CH2:1][CH:2]([CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 7509Benzyl mercaptanHCID 10947302Dibenzyl 2-methylenepentanedioate

Product 1

HCID 22460508Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioateYield 90%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of dibenzyl 2-methylenepentanedioate (12.16 g, 37.5 mmol) in acetone (100 mL), was added benzylmercaptan (9.31 g, 75.0 mmol) and 4-dimethylaminopyridine (0.46 g, 3.75 mmol) with stirring. The reaction mixture was refluxed for 16 hours. The cooled solution was concentrated under reduced pressure and purified by column chromatography to yield 15.2 g (90%) of clear oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. concentrationThe cooled solution was concentrated under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-73390a277c614993aa728725c0121753
Source dataset
uspto-grants-2002_05
Patent number
US06395718B1

Reaction notes

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