Ethyl Acetate → {6-[(2-Fluorophenyl)methoxy]pyridin-3-yl}methanol

HRID 1794081Notes

Reaction equation

HRID 1794081 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 222200456-[(2-Fluorophenyl)methoxy]pyridine-3-carboxylic acid

Product 1

HCID 22220075{6-[(2-Fluorophenyl)methoxy]pyridin-3-yl}methanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

to a stirred solution of 6-(2-fluorobenzyloxy)nicotinic acid (0.89 g) in THF (10 ml) at 0° C. under Ar was added dropwise a solution of lithium aluminium hydride (1.0 M, 5.5 ml). The mixture was warmed to room temperature and stirred for 2 h. Saturated potassium sodium tartrate solution (1 ml) was added to the mixture followed by ethyl acetate (10 ml). The mixture was stirred for 30 min, filtered and concentrated in vacuo to give the product as a clear oil (0.63 g) which was used without further purification; δH (400 MHz, CDCl3) 8.14 (1H, d, J 1.5 Hz), 7.63 (1H, dd, J 8.5, 2.5 Hz), 7.49 (1H, dt, J 7.5, 1 Hz), 7.29 (1H, m), 7.13 (1H, dt, J 7.5, 1 Hz), 7.02 (1H, dt, J 10, 1 Hz), 6.81 (1H, d, J 8 Hz), 5.45 (2H, s) and 4.63 (2H, s); LC 73%, 2.24 min.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d39c6df19fb040bc8ffdbe3a44beb477
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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