Water → 1-(4-Chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl) cyclopropane

HRID 963809Notes

Reaction equation

HRID 963809 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:11]=[C:12]([F:17])[C:13](OC)=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:11]=[C:12]([F:17])[CH2:13][OH:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 541414971-(4-Chlorophenyl)-1-(2-fluoro-2-(methoxycarbonyl)ethenyl)cyclopropane

Product 1

HCID 543549731-(4-Chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl) cyclopropaneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-(4-Chlorophenyl)-1-(2-fluoro-2-(methoxycarbonyl)ethenyl)cyclopropane prepared as described In Example 1 (0.73 g) in dry diethyl ether (10 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (0.18 g) in dry diethyl ether at 0° C. Stirring was continued during 40 min, while the mixture warmed to room temperature. Water (20 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 residue was chromatographed on silica using diethyl ether/hexane (1:2) to yield 1-(4-chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl) cyclopropane (0.56 g, 86%).

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 residue was chromatographed on silica

Sources & evidence

ORD record
ord-880d24224df446fc84bd754957983b96
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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