Sodium borohydride → HCID 86680619, compound

HRID 1497448Notes

Reaction equation

HRID 1497448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14](=[O:16])[CH3:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([OH:16])[CH3:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 82078553HCID 82078553, compound

Product 1

HCID 86680619HCID 86680619, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 1-(5-(4-fluorophenyl)pyridin-2-yl)ethanone (0.75 g, 3.48 mmol) in MeOH (20 mL) was added NaBH4 (0.264 g, 6.97 mmol) and the contents stirred at 0-5° C. for 2 h. The mixture was diluted with ethyl acetate (150 mL) and then washed with ammonium chloride solution (2×50 mL) and brine solution (2×100 mL). The organic layer was dried over sodium sulphate and distilled off to obtain the crude compound. The crude product was purified by flash chromatography (230-400; 35% ethyl acetate in hexane) to afford 1-(5-(4-fluorophenyl)pyridin-2-yl)ethanol (0.45 g, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.74 (s, 1H), 8.03 (dd, 1H), 7.74 (t, 2H), 7.56 (d, 1H), 7.30 (t, 2H), 5.35 (d, 1H), 4.74 (q, 1H), 1.38 (d, 3H); LC-MS m/z calcd for [M+H]+ 218.25. found 218.0.

Workup

  1. washwashed with ammonium chloride solution (2×50 mL) and brine solution (2×100 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. distillationdistilled off
  4. customto obtain the crude compound
  5. customThe crude product was purified by flash chromatography (230-400; 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-783737bf874046bfac4df84d45cebf0e
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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