Sodium borohydride → (4-(4-Chloro-2-fluorophenyl)-2-methylpyridin-3-yl)methanol

HRID 2369554Notes

Reaction equation

HRID 2369554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[O:15])=[C:12]([CH3:16])[N:11]=[CH:10][CH:9]=2)=[C:4]([F:17])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[C:12]([CH3:16])[C:13]=2[CH2:14][OH:15])=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866959504-(4-Chloro-2-fluorophenyl)-2-methylnicotinaldehyde

Product 1

HCID 86695951(4-(4-Chloro-2-fluorophenyl)-2-methylpyridin-3-yl)methanolYield 248.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-chloro-2-fluorophenyl)-2-methylnicotinaldehyde (60 mg, 0.240 mmol) in MeOH (2 mL) at 0° C., was added NaBH4 (27.3 mg, 0.721 mmol) and the solution stirred for 3 h at RT. The mixture was concentrated and diluted with EtOAc (15 mL) and water (10 mL). The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford (4-(4-chloro-2-fluorophenyl)-2-methylpyridin-3-yl)methanol (0.15 g, 0.596 mmol, 89% yield) as a brown solid. LCMS (ESI) m/e 252.03 [(M+H)+, calcd for C13H12ClFNO 252.1]; LC/MS retention time (Method G): tR=0.80 min.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc (15 mL) and water (10 mL)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e71eb39df304392918df5b2da984f91
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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