Sodium borohydride → [3-Fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol

HRID 426231Notes

Reaction equation

HRID 426231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>C(O)C.CO.[Cl-].[NH4+]>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH:9]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 591848623-Fluoro-5-(4-methoxy-benzylamino)-benzaldehyde

Product 1

HCID 59184687[3-Fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanolYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

3-Fluoro-5-(4-methoxy-benzylamino)-benzaldehyde (crude product) was dissolved in anhydrous ethanol (40 ml) and cooled in an ice bath. Sodium borohydride (800 mg, 21 mmol) was then added with stirring. After 1 hr., the mixture was diluted with methanol and excess ammonium chloride was added. After stirring for 1 hr. at room temperature, the mixture was evaporated in vacuo and coevaporated with methanol several times. The residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:4 to 1:1)) to afford 2.16 g (39%) of [3-fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol as a white solid. m.p. 93° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. stirringAfter stirring for 1 hr
  4. customat room temperature, the mixture was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:4 to 1:1))

Sources & evidence

ORD record
ord-8b0a988cf5eb48d798566bba8253533f
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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