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

HRID 1672631Notes

Reaction equation

HRID 1672631 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}methanolYield 86.6%

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 from Example 29A 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 then taken up in water and dichloromethane. The aqueous phase is then 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% yield) of a colorless solid are obtained.

Workup

  1. customAfter reaction
  2. concentrationthe mixture is concentrated to dryness
  3. extractionThe aqueous phase is then 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)

Sources & evidence

ORD record
ord-2972fe19eb314e09a9e1aadfd3b50740
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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