Sodium borohydride → [6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

HRID 2194897Notes

Reaction equation

HRID 2194897 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:15]([C:16](OC)=[O:17])=[CH:14][N:13]=1.[BH4-].[Na+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[CH:14][C:15]([CH2:16][OH:17])=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67447798Methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate

Product 1

HCID 67448255[6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate (1 eq.) from step 1, in MeOH (0.14M) was added portion wise sodium borohydride (9.3 eq.). The mixture was stirred at 65° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 20% afforded the desired compound as an oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/EtOAc 20%

Sources & evidence

ORD record
ord-709134f9f9724bd6b5db0381c8e33ee6
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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