Cyclopropyl methyl ketone → 1-Cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one

HRID 2061191Notes

Reaction equation

HRID 2061191 reaction equation
[H-].[Na+].[CH:3]1([C:6](=[O:8])[CH3:7])[CH2:5][CH2:4]1.[C:9]([S:13][CH3:14])([S:11][CH3:12])=S>CN(C=O)C>[CH:3]1([C:6](=[O:8])[CH:7]=[C:9]([S:13][CH3:14])[S:11][CH3:12])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 16840Dimethyl trithiocarbonateHCID 24758Sodium hydride

Product 1

HCID 581806291-Cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of NaH (240 mg, 6.0 mmol, 60% in mineral oil) and 1-cyclopropylethanone (168.2 mg, 2.0 mmol) in DMF (1 mL) was added dimethyl carbonotrithioate (304.3 mg, 2.2 mmol) at rt. The reaction was quenched with water after 3 h and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to yield crude 1-cyclopropyl-3,3-bis(methylthio)prop-2-en-1-one 30 which was purified by flash chromatography on silica with 15% EtOAc in hexanes as eluant. 1H NMR (400 MHz, CDCl3) δ 6.14 (s, 1H), 2.41 (s, 3H), 2.40 (s, 3H), 1.81 (m, 1H), 1.00 (m, 2H), 0.77 (m, 2H). MS m/z 189.0 (M+1).

Workup

  1. customThe reaction was quenched with water after 3 h
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ca0841d9ae6641eb837b34173c1dc86e
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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