Sodium borohydride → HCID 67177503, compound

HRID 885209Notes

Reaction equation

HRID 885209 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:11]2([CH2:14][CH:15]=[O:16])[CH2:13][CH2:12]2)[CH:7]=[C:8]([F:10])[CH:9]=1>CO>[F:3][C:4]1[CH:5]=[C:6]([C:11]2([CH2:14][CH2:15][OH:16])[CH2:12][CH2:13]2)[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86638535HCID 86638535, compound

Product 1

HCID 67177503HCID 67177503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of sodium borohydride (1.0 g) in methanol (20 ml) under an argon atmosphere was added slowly a solution of [1-(3,5-difluoro-phenyl)-cyclopropyl]-acetaldehyde in methanol (10 ml). Stirring was continued at room temperature overnight, then the reaction mixture was quenched by slow addition of water. Methanol was evaporated and the aqueous phase was extracted with ethyl acetate twice. The combined organic layers were dried over MgSO4 and concentrated to give 2-[1-(3,5-difluoro-phenyl)-cyclopropyl]-ethanol as yellow liquid (2.37 g). 1H-NMR (300 MHz, CDCl3, δ): 0.76-0.86 (m, 4H), 1.85 (t, J=7 Hz, 2H), 3.61-3.62 (m, 2H), 6.60-6.67 (m, 1H), 6.78-6.85 (m, 2H).

Workup

  1. customthe reaction mixture was quenched by slow addition of water
  2. customMethanol was evaporated
  3. extractionthe aqueous phase was extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dfae39741f2341c795054b2adce69eda
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

Loading…