Sodium borohydride → HCID 86680624, compound

HRID 1497454Notes

Reaction equation

HRID 1497454 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:18])[CH3:17])=[N:14][CH:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>C1COCC1.CO.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([CH:16]([OH:18])[CH3:17])=[N:14][CH:15]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86680623HCID 86680623, compound

Product 1

HCID 86680624HCID 86680624, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(5-(4-nitrophenyl)pyridin-2-yl)ethanone (100 mg, 0.4 mmol) in THF (2 mL) and methanol (2 mL) was added NaBH4 (3 mg, 0.8 mmol) at rt and the reaction was stirred at rt for about 5 min. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain 1-(5-(4-nitrophenyl)pyridin-2-yl)ethanol as off white solid (100 mg, 100% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.88 (d, 1H), 8.31 (d, 2H), 8.19 (dd, 1H), 8.01 (d, 2H), 7.64 (d, 1H), 5.43 (d, 1H), 4.78 (t, 1H), and 1.38 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic extracts were washed with brine solution (10 mL), organic layer
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a9fea8aa5c454c1aa942f48d82b693c5
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

Loading…