Sodium borohydride → (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-ol

HRID 1904981Notes

Reaction equation

HRID 1904981 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[O:14])=[CH:8][CH:7]=1)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([C:15]([F:16])([F:17])[F:18])[CH2:13][OH:14])=[CH:10][CH:11]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 107995612-(4Ethoxyphenyl)-3,3,3-trifluoropropanal

Product 1

HCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-olYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A hundred milligrams of sodium borohydride was added to a solution of 1.04 g of 2-(4ethoxyphenyl)-3,3,3-trifluoropropanal in 15 ml of ethanol with ice-cooling. The reaction solution was stirred at room temperature for 4hours. Thereafter, the reaction mixture was poured into ice water and extracted twice with ethyl acetate. The ethyl acetate layers were combined and washed with dilute HCl and saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography on silica gel [eluted with n-hexane/ethyl acetate (4:1) mixture] to obtain 0.77 g of the desired compound.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. washwashed with dilute HCl and saturated sodium chloride solution successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7b18ff902e134bc6b370c0d93c1b3f1d
Source dataset
uspto-grants-1989_06
Patent number
US04840971

Reaction notes

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