Dichloromethane → HCID 19877590, compound

HRID 1886252Notes

Reaction equation

HRID 1886252 reaction equation
[CH2:1](Cl)Cl.C[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16][CH2:17][C:18](=[O:23])[CH2:19][C:20]([O-:22])=[O:21])[CH:10]=[CH:9]2.B(Br)(Br)Br>CO>[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16][CH2:17][C:18](=[O:23])[CH2:19][C:20]([O:22][CH3:1])=[O:21])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 19877617HCID 19877617, compound

Product 1

HCID 19877590HCID 19877590, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A dry methylene chloride solution of 102.8 mg (0.34 mmol) of 4-(6-methoxy-2-naphthylthio)-3-oxobutanoate was cooled to -78° C., one hundred (100) μl (0.97 mmol) of boron tribromide was added, and the reaction was carried out from -78° C. to room temperature for 2 hours. Then dry methanol (3 ml) was added, and the mixture was stirred over one day and night at room temperature. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the desired sulfideketone derivative was obtained by silica gel column chromatography. Yield: 81.8 mg (83%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customthe desired sulfideketone derivative was obtained by silica gel column chromatography

Sources & evidence

ORD record
ord-a495fdfa0540460bbb3f62e62270481a
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

Loading…