Water → HCID 54135764, compound

HRID 1418058Notes

Reaction equation

HRID 1418058 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:16]2[CH2:18][CH2:17]2)[CH:9]=[C:10]([F:15])[C:11](OC)=[O:12])=[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]([CH:8]([CH:16]2[CH2:17][CH2:18]2)[CH:9]=[C:10]([F:15])[CH2:11][OH:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54287809HCID 54287809, compound

Product 1

HCID 54135764HCID 54135764, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methyl 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enoate prepared as described in Example 1 (0.91 g) in dry diethyl ether (20 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (0.34 g) in dry diethyl ether (25 ml) at 0° C. Stirring was continued during 40 minutes, while the mixture warmed to room temperature. Water (4 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 (2:3) to yield 4-(4-chlorophenyl)-4-cyclopropyl-2-fluorobut-2-enol (0.61 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-c3a1e65f589a4048869d463a196487c0
Source dataset
uspto-grants-1999_03
Patent number
US05880162

Reaction notes

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