Hydrochloric Acid → [6-(Trifluoromethyl)pyridine-2,3-diyl]dimethanol

HRID 225545Notes

Reaction equation

HRID 225545 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[N:6]=1)=O.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].Cl>CO>[OH:12][CH2:11][C:10]1[C:5]([CH2:3][OH:2])=[N:6][C:7]([C:15]([F:18])([F:16])[F:17])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57753443Dimethyl 6-(trifluoromethyl)pyridine-2,3-dicarboxylate

Product 1

HCID 57753369[6-(Trifluoromethyl)pyridine-2,3-diyl]dimethanolYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6 mmol 6-trifluoromethyl-pyridine-2,3-dicarboxylic acid dimethyl ester in 10 ml methanol was cooled to 0° C. 12 mmol of sodium borohydride and 6 mmol of calcium chloride were added and the resulting mixture stirred overnight at room temperature. After cooling again to 0° the reaction mixture was neutralized by addition of 5 ml 3M aqueous hydrochloric acid. The mixture is concentrated, diluted with water and extracted 3 times with ethyl acetate. The crude compound is purified by chromatography (SiO2; ethyl acetate/n-heptane 1:1) to give the title compound as a yellow oil. Yield: 72%. MS (m/e): 208.1 (MH+, 100%).

Workup

  1. temperatureAfter cooling again to 0° the reaction mixture
  2. concentrationThe mixture is concentrated
  3. additiondiluted with water
  4. extractionextracted 3 times with ethyl acetate
  5. customThe crude compound is purified by chromatography (SiO2; ethyl acetate/n-heptane 1:1)

Sources & evidence

ORD record
ord-3dcd32769cb149d39a496780e0e8ed49
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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