Benzyl mercaptan → Dibenzyl 2-[(benzylsulfanyl)methyl]pentanedioate

HRID 1075468Notes

Reaction equation

HRID 1075468 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.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])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 7509Benzyl mercaptanHCID 10947302Dibenzyl 2-methylenepentanedioate

Product 1

HCID 15410799Dibenzyl 2-[(benzylsulfanyl)methyl]pentanedioateYield 90.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

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. 1H NMR (CDCl3): δ 2.0 (m, 2H), 2.3 (m, 2H), 2.5 (m, 1H), 2.6 (m 2H), 3.6 (s, 2H), 4.9 (s, 2H), 5.0 (m, 2H), 7.2-7.5 (m, 15H).

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-9b8dc6e65d324c39b7c51073f374266e
Source dataset
uspto-grants-1999_05
Patent number
US05902817

Reaction notes

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