Ethanol → alpha-Methyl-3-pyridinemethanol

HRID 2294939Notes

Reaction equation

HRID 2294939 reaction equation
[BH4-].[Na+].C([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)(=O)C.[CH2:12]([OH:14])[CH3:13]>>[OH:14][CH:12]([C:9]1[CH:8]=[N:7][CH:6]=[CH:11][CH:10]=1)[CH3:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 142862-AcetylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 101192alpha-Methyl-3-pyridinemethanol

Procedure

Sodium borohydride (1.75 g) was added in portions to a stirred solution of acetylpyridine (12.1 g) in ethanol (100 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 20 min, then concentrated under reduced pressure to remove ethanol. The thick residue was diluted with 300 mL of dichloromethane, 25 mL of water and 5 mL of 20% NaOH. The aqueous layer was saturated with sodium chloride, and extracted with ethyl acetate (4×150 mL). The combined organic extracts were dried (MgSO4) and concentrated. Evaporative distillation of the crude oily product (14.0 g) at 1 mm, oven temperature 85°-95° C. gave 11.4 g of 3-(1-hydroxyethyl)pyridine as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove ethanol
  3. additionThe thick residue was diluted with 300 mL of dichloromethane, 25 mL of water and 5 mL of 20% NaOH
  4. extractionextracted with ethyl acetate (4×150 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. distillationEvaporative distillation of the crude oily product (14.0 g) at 1 mm, oven temperature 85°-95° C.

Sources & evidence

ORD record
ord-fed419d16cff4e02bbe0885d234b1529
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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