Water → (6-Ethoxypyridin-2-yl)methanol

HRID 1171762Notes

Reaction equation

HRID 1171762 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH3:16])[N:9]=1)=O)C.O>CCO>[CH2:15]([O:14][C:10]1[N:9]=[C:8]([CH2:6][OH:5])[CH:13]=[CH:12][CH:11]=1)[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53393170Ethyl 6-ethoxypyridine-2-carboxylate

Product 1

HCID 53393171(6-Ethoxypyridin-2-yl)methanolYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (5.7 g, 151 mmol) was added in portions during 35 minutes to 6-ethoxy-pyridine-2-carboxylic acid ethyl ester (1.5 g, 7.5 mmol) in EtOH (75 mL). The resulting mixture was stirred at ambient temperature for two days. Water was added and the mixture was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered and then concentrated to give the title product (0.85 g) in 74% yield as an oil. This material was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5910011422294b90a426425b9aeeeb51
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

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