Acetone → HCID 9817284, compound

HRID 1075465Notes

Reaction equation

HRID 1075465 reaction equation
[CH2:1]=[C:2]([CH2:13][CH2:14][C:15]([O:17]CC1C=CC=CC=1)=[O:16])[C:3]([O:5]CC1C=CC=CC=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]([OH:17])=[O:16])[C:3]([OH:5])=[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 9817284HCID 9817284, compoundYield 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. 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-4e5705c7eaa84bd1a1c01543d8456bec
Source dataset
uspto-grants-1999_05
Patent number
US05902817

Reaction notes

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