Triethylamine → 2-Cyano-5-hydroxymethylpyridine

HRID 1990749Notes

Reaction equation

HRID 1990749 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][N:4]=1)#[N:2].CCN(CC)CC.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1>[OH:8][CH2:7][C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 122519662-Cyano-5-hydroxymethylpyridineYield 36.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-cyanonicotinic acid (12 g, 0.081 mol; see step (i) above) in THF at 0° C., Et3N (12.4 mL, 0.0892 mol) was added followed by ethyl chloroformate (8.53 mL, 0.0892 mol). The reaction mixture was stirred for 15 min and NaBH4 (6.14 g, 0.162 mol) was added. Then the mixture was stirred at RT overnight, quenched with water and extracted with methylene chloride. The organic layer was concentrated and purified by column chromatography to yield 4 g (20%) of the alcohol.

Workup

  1. stirringThen the mixture was stirred at RT overnight
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. concentrationThe organic layer was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-d3f66a429a8043479778b68b73f7d06f
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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