Diethyl Ether → 6-Ethylthio-3-hepten-2-one

HRID 661772Notes

Reaction equation

HRID 661772 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:8][C:9](=[O:11])[CH3:10])C=CC=CC=1.[CH2:24]([S:26][CH:27]([CH3:31])[CH2:28][CH:29]=O)[CH3:25].CCCCCC.CCOCC>ClCCl>[CH2:24]([S:26][CH:27]([CH3:31])[CH2:28][CH:29]=[CH:8][C:9](=[O:11])[CH3:10])[CH3:25]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 1601413-(Ethylsulfanyl)butanal

Product 1

HCID 544576116-Ethylthio-3-hepten-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Triphenylphosphoranylidene-2-propanone (12.77 g, 40.0 mmol) is added to a solution of 3-(ethylthio)butyraldehyde (5.30 g, 40.0 mmol) in dichloromethane (100 ml) and the mixture is heated under reflux for 24 hours. The reaction mixture is cooled to room temperature, and the solvent evaporated in vacuo to give a beige solid. The crude product is taken up in a 1:1 mixture of hexane:ether (the insoluble material is discarded), and then concentrated under reduced pressure to give an orange oil which is further purified by column chromatography on silica gel to give 6-(ethylthio)hept-3-en-2-one as a yellow oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 24 hours
  3. customthe solvent evaporated in vacuo
  4. customto give a beige solid
  5. concentrationthen concentrated under reduced pressure
  6. customto give an orange oil which
  7. customis further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3c0061b074da4c3bb8dba46c2fd833e8
Source dataset
uspto-grants-2011_12
Patent number
US08084649B2

Reaction notes

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