Sodium borohydride → HCID 86680621, compound

HRID 1497450Notes

Reaction equation

HRID 1497450 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12](=[O:14])[CH3:13])=[N:10][CH:11]=2)=[CH:2]1.[BH4-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([OH:14])[CH3:13])=[N:10][CH:11]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86680620HCID 86680620, compound

Product 1

HCID 86680621HCID 86680621, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(5-(furan-3-yl)pyridin-2-yl)ethanone (0.2 g, 1.0752 mmol) in MeOH (10 ml) was added sodium borohydride (0.0795 g, 2.150 mmol) at 0° C., the reaction mixture warmed to room temperature and was stirred for 2 h. The reaction mixture was evaporated under reduced pressure to remove the methanol, diluted with water (15 mL), extracted with ethyl acetate (200 mL), dried over sodium sulphate and concentrated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 20% ethyl acetate and hexane to give 1-(5-(furan-3-yl)pyridin-2-yl)ethanol as a colorless liquid (0.150 g, 73% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 7.76 (t, 2H), 7.52 (s, 1H); 7.28 (t, 1H), 6.71 (s, 1H), 4.91 (d, 1H), 4.14-4.07 (m, 1H), 1.52 (d, 3H): LC-MS m/z calcd for [M+H]+ 189.08. found 190.0.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto remove the methanol
  3. additiondiluted with water (15 mL)
  4. extractionextracted with ethyl acetate (200 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain crude product
  8. customThe crude product was purified by Biotage Isolera® One column (

Sources & evidence

ORD record
ord-23008e35833441b994b4866fddb7fb60
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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