Water → HCID 53748107, compound

HRID 1418063Notes

Reaction equation

HRID 1418063 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:18]2[CH2:20][CH2:19]2)[CH:13]=[C:14]([F:17])[CH2:15][OH:16])=[CH:8][CH:7]=1.O>C1C=CC=CC=1.N1C=CC=CC=1>[C:1]([O:16][CH2:15][C:14]([F:17])=[CH:13][CH:12]([C:9]1[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=1)[CH:18]1[CH2:19][CH2:20]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 54135764HCID 54135764, compound

Product 1

HCID 53748107HCID 53748107, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Acetyl chloride (1.2 ml) was slowly added to a stirred solution of 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enol (Example 6) (0.51 g) in benzene (30 ml) and pyridine (0.24 ml) at 0° C. and stirring was continued for 24 hours while the mixture warmed to room temperature. Water (2 ml) was added, and the mixture was extracted with diethyl ether (3×20 ml). The combined organic layers were washed with water (3×10 ml), dried and evaporated under reduced pressure. The residual oil was chromatographed on silica gel using diethyl ether/hexane (1:4) to yield 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enyl acetate (0.46 g, 78%).

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×20 ml)
  2. washThe combined organic layers were washed with water (3×10 ml)
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-dad3fcf4c7e74646bc49eccc8885bd77
Source dataset
uspto-grants-1999_03
Patent number
US05880162

Reaction notes

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