Methanol → Ethyl 4-(2'-fluoro-4-biphenylyl)-4-hydroxy-butyrate

HRID 2397422Notes

Reaction equation

HRID 2397422 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1.CO.[BH4-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 21437951Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate

Product 1

HCID 21437975Ethyl 4-(2'-fluoro-4-biphenylyl)-4-hydroxy-butyrate

Procedure

To a solution of 15 gm (0.05 mol) of ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate in 100 ml of methanol 1.9 gm (0.05 mol) of sodium borohydride were added at a temperature between 0° and 5° C., while stirring. The precipitate was vacuum-filtered off and dissolved in ether. The ethereal solution was washed with an aqueous sodium bicarbonate solution and then with water, dried and evaporated. The residual oil was recrystallized from cyclohexane. Yield: 12 gm (79.5% of theory), m.p. 61°-62° C.

Workup

  1. filtrationThe precipitate was vacuum-filtered off
  2. dissolutiondissolved in ether
  3. washThe ethereal solution was washed with an aqueous sodium bicarbonate solution
  4. dry with materialwith water, dried
  5. customevaporated
  6. customThe residual oil was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-0fe636e95d404589b4d81944cbf783a3
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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