Dimethyl Sulfide → Propyl 3-oxocyclobutanecarboxylate

HRID 2048378Notes

Reaction equation

HRID 2048378 reaction equation
[O:1]=[O+][O-].C=[C:5]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[CH2:6]1.CSC>CO>[O:1]=[C:5]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[CH2:6]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 45090160Cyclobutanecarboxylic acid, 3-methylene-, propyl ester

Product 1

HCID 67008885Propyl 3-oxocyclobutanecarboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ozone gas was blown into a solution (200 mL) of propyl 3-methylidenecyclobutanecarboxylate (15 g) in methanol at −78° C. for 2 hr. Dimethyl sulfide (21 g) was added to the reaction mixture at the same temperature, and the mixture was warmed to room temperature over 1 hr. The obtained mixture was concentrated and purified by silica gel column chromatography to give the title compound as a colorless oil (13 g, 88%).

Workup

  1. concentrationThe obtained mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e9bb5d4bbd84741914c35d8c03a1471
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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