Sodium borohydride → HCID 178520638, compound

HRID 2399215Notes

Reaction equation

HRID 2399215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH:24]=[O:25])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178520637HCID 178520637, compound

Product 1

HCID 178520638HCID 178520638, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 0.44 g of 3-[trans-4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexyl]propanal in 20 ml of methanol/water (vol. 4:1) and 15 ml of dioxan is treated portionwise with 0.10 g of sodium borohydride. The reaction mixture is stirred at room temperature for 0.75 hour and concentrated. The residue is treated with water and extracted with diethyl ether. The ether phase is washed with water, dried over sodium sulphate, filtered and evaporated. 0.36 g of 3-[trans-4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexyl]propanol is obtained.

Workup

  1. concentrationconcentrated
  2. additionThe residue is treated with water
  3. extractionextracted with diethyl ether
  4. washThe ether phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3b6163c6f28c4464847990d196772bbb
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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