Sodium borohydride → E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol

HRID 1927412Notes

Reaction equation

HRID 1927412 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:8]([CH:11]=1)[CH:9]=[O:10]>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7](/[CH:12]=[CH:13]/[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:8]([CH2:9][OH:10])[CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57831341E-5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehyde

Product 1

HCID 57831377E-{5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]phenyl}methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.73 g (45.60 mmol) of sodium borohydride are added in portions to a solution of 7.79 g (30.40 mmol) of E-5-fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehyde in 500 ml of methanol at 0° C., and the mixture is stirred at room temperature for 2 hours. After reaction is complete, the mixture is concentrated to dryness and the residue is taken up in water and dichloromethane. The aqueous phase is extracted twice more with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). 6.8 g (85% of theory) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe mixture is concentrated to dryness
  3. extractionThe aqueous phase is extracted twice more with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1)
  8. custom6.8 g (85% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-bcd22c98731b487abe3938b40b40cdf0
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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