Chloride → Z-1-hydroxymethyl-1-(4-fluorophenyl)-2-(3-cyclohexenyl)ethene

HRID 654465Notes

Reaction equation

HRID 654465 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[CH:13]/[CH:14]2[CH2:19][CH2:18][CH:17]=[CH:16][CH2:15]2)/[CH:11]=[O:12])=[CH:6][CH:5]=1.O.[Cl-]>[OH-].[Na+].CO>[OH:12][CH2:11]/[C:10](/[C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)=[CH:13]\[CH:14]1[CH2:19][CH2:18][CH:17]=[CH:16][CH2:15]1

Participants

7

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 4311764Sodium borohydrideHCID 21615834Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenal

Product 1

HCID 19774242Z-1-hydroxymethyl-1-(4-fluorophenyl)-2-(3-cyclohexenyl)etheneYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2 g of sodium borohydride dissolved in a little 10% strength sodium hydroxide solution are added to a solution of 34 g of Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenal in 200 ml of methanol. After the reaction mixture has been stirred for 18 hours at room temperature, 100 ml of water are added to the solution and the chloride. The organic phase isolated is then dried over sodium sulfate and evaporated down. 34 g (99%) of Z-1-hydroxymethyl-1-(4-fluorophenyl)-2-(3-cyclohexenyl)ethene are obtained.

Workup

  1. customThe organic phase isolated
  2. dry with materialis then dried over sodium sulfate
  3. customevaporated down

Sources & evidence

ORD record
ord-84f9f897cadd4b0e8661708c6d9e1d1e
Source dataset
uspto-grants-1992_07
Patent number
US05132318

Reaction notes

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