Water → HCID 14497611, compound

HRID 2372330Notes

Reaction equation

HRID 2372330 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[CH:13]\[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])/[CH:11]=[O:12])=[CH:6][CH:5]=1.O>[OH-].[Na+].C(O)(C)C>[F:3][C:4]1[CH:5]=[CH:6][C:7](/[C:10](=[CH:13]\[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])/[CH2:11][OH:12])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 49817780(2E)-3-(2-Chlorophenyl)-2-(4-fluorophenyl)prop-2-enal

Product 1

HCID 14497611HCID 14497611, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

7.3 g of sodium borohydride, which has been dissolved in a little 10% strength sodium hydroxide solution are added to a solution of 150 g of E-2-(4-fluorophenyl)-3-(2-chlorophenyl)-propenal (prepared as described in Example A) in 600 ml of isopropanol at 0° C. After the reaction mixture has been stirred for two hours at room temperature, 300 ml of water are added to the solution and the resulting emulsion is extracted by shaking with methylene chloride. The organic phase isolated is then dried over sodium sulfate and evaporated down. 150.7 g (100%) of E-2-(4-fluorophenyl)-3-(2-chlorophenyl)-prop-2-enol are obtained.

Workup

  1. extractionthe resulting emulsion is extracted
  2. stirringby shaking with methylene chloride
  3. customThe organic phase isolated
  4. dry with materialis then dried over sodium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-9f7a64c4be44472c83cbbbfd7f5eb4d8
Source dataset
uspto-grants-1992_03
Patent number
US05098917

Reaction notes

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