Water → 1-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropane

HRID 963817Notes

Reaction equation

HRID 963817 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH:15]=[C:16]([F:19])[CH2:17][OH:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.O>C1C=CC=CC=1.N1C=CC=CC=1>[C:1]([O:18][CH2:17][C:16]([F:19])=[CH:15][C:12]1([C:9]2[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=2)[CH2:13][CH2:14]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 543549731-(4-Chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl) cyclopropane

Product 1

HCID 543111381-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropaneYield 87%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.72 ml) was slowly added to a stirred solution of 1-(4-chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl)cyclopropane (Example 9) (0.36 g) in benzene (20 ml) and pyridine (0.14 ml) at 0° C., and stirring was continued for 24 h while the mixture warmed to room temperature. After addition of water (10 ml), the mixture was extracted with diethyl ether (3×20 ml) and the combined organic layers were washed with water (3×10 ml) and evaporated under reduced pressure. The residue was chromatographed on silica using diethyl ether/hexane (1:9) to yield 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-chlorophenyl)cyclopropane (0.37 g, 87%).

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. customevaporated under reduced pressure
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-05b2ff4f771a4e3fb95b68d57bca1849
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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