Water → HCID 67399482, compound

HRID 70509Notes

Reaction equation

HRID 70509 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([C:11](OCC)=[O:12])[CH:8]=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17].O>CO>[CH3:3][O:4][C:5]1[N:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:6]=1[C:16]([F:19])([F:17])[F:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67399178Ethyl 6-methoxy-5-(trifluoromethyl)pyridine-2-carboxylate

Product 1

HCID 67399482HCID 67399482, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (405 mg) was added to a solution of ethyl 6-methoxy-5-(trifluoromethyl)pyridine-2-carboxylate (670 mg, described in WO 2005058830) in methanol (20 mL) under ice-cooling, and the mixture was stirred at room temperature for two hours. The reaction solution was poured into water, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure to give [6-methoxy-5-(trifluoromethyl)pyridin-2-yl]methanol (540 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationafter which the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49910b10adba4dcebc685161501d4e6f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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