Methyl vinyl ketone → HCID 12046648, compound

HRID 1626089Notes

Reaction equation

HRID 1626089 reaction equation
[C:1]([O:5][C:6](=[O:11])[CH:7]=S(C)C)([CH3:4])([CH3:3])[CH3:2].[CH3:12][C:13](=[O:16])[CH:14]=[CH2:15]>ClCCl>[C:1]([O:5][C:6]([C@@H:7]1[CH2:15][C@H:14]1[C:13](=[O:16])[CH3:12])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 10997584HCID 10997584, compound

Product 1

HCID 12046648HCID 12046648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (dimethyl-λ4-sulfanylidene)-acetic acid tert-butyl ester (6.3 g, 35.7 mmol) (CAS 195453-96-4; K. Saigo et al., J. Org. Chem. 2006, 71, 1633-1639) in dichloromethane (36 ml) was treated dropwise at 15° C. with but-3-en-2-one (2.64 g, 3.1 ml, 35.7 mmol) keeping the internal temperature below 27° C. The yellow mixture was stirred overnight at room temperature. For the workup, all volatiles were evaporated to give a yellow oil. The crude oil was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 80:20 as the eluent. The (1R,2R)-rel-2-acetyl-cyclopropanecarboxylic acid tert-butylester was obtained as a colorless oil (5.48 g, 83% yield). MS (ISP): m/z=185.0 [M+H]+.

Workup

  1. customthe internal temperature below 27° C
  2. customFor the workup, all volatiles were evaporated
  3. customto give a yellow oil
  4. customThe crude oil was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 80:20 as the eluent

Sources & evidence

ORD record
ord-a408920545244be98c8273969ff02625
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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