Sodium borohydride → HCID 57706281, compound

HRID 1662357Notes

Reaction equation

HRID 1662357 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][C:11]=1[O:18][C:19]([F:22])([F:21])[F:20].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[O:18][C:19]([F:20])([F:21])[F:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57706456HCID 57706456, compound

Product 1

HCID 57706281HCID 57706281, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 46.1 (0.165 g, 0.53 mmol) in MeOH (6 mL) was added sodium borohydride (0.040 g, 1.05 mmol) in one portion at room temperature. The mixture was stirred for 30 minutes, quenched with 1 N HCl, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The crude product was chromatographed on silica gel (0-30% EtOAc/hexane) to afford 46.2 (0.164 g, 99%) as a colorless oil.

Workup

  1. customquenched with 1 N HCl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-cfe698591fe04542b460ce62d9585a90
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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