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

HRID 536081Notes

Reaction equation

HRID 536081 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-5f39c74ac32947c68336dee9a8c45c0b
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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