Water → 2-(6-(2-Fluorophenyl)pyridin-3-yloxy)ethanol

HRID 1896701Notes

Reaction equation

HRID 1896701 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[CH:10][CH:11]=1.[BH4-].[Li+].O>C1COCC1>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[N:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][OH:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 69105901(6-(2-Fluorophenyl)pyridin-3-yloxy)acetic acid methyl ester

Product 1

HCID 691055892-(6-(2-Fluorophenyl)pyridin-3-yloxy)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 675 mg (2.58 mmol) of (6-(2-fluorophenyl)pyridin-3-yloxy)acetic acid methyl ester and 112.5 mg (5.17 mmol) of lithium borohydride were stirred in 20 ml of THF at 60° C. for 2 h. After cooling, the mixture was cautiously hydrolyzed with water and concentrated, and water and ethyl acetate were added. The organic phase was separated, washed with water and concentrated. Yield: 350 mg (58%).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated
  3. additionwater and ethyl acetate were added
  4. customThe organic phase was separated
  5. washwashed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e3327b8911e49db8f5f6fd74795802f
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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