Hydrochloric Acid → [2-(Pyridin-2-yl)-1,3-thiazol-4-yl]methanol

HRID 1871033Notes

Reaction equation

HRID 1871033 reaction equation
CO.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=1.[BH4-].[Na+].Cl>O1CCCC1.O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 10082761Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

Product 1

HCID 10750266[2-(Pyridin-2-yl)-1,3-thiazol-4-yl]methanolYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

40 ml of methanol were added slowly to a mixture of 9.3 g of the ester of Stage C and 4.1 g of sodium borohydride in 100 ml of tetrahydrofuran and the mixture was refluxed for 2 hours. The reaction medium was allowed to return to ambient temperature and was poured into water and neutralized using N hydrochloric acid. Extraction was carried out with dichloromethane and the organic phase was dried. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica (eluant: AcOEt-CH2Cl2 1-1) to obtain 5.8 g of the expected product melting at 100° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customto return to ambient temperature
  3. extractionExtraction
  4. customthe organic phase was dried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was chromatographed on silica (eluant: AcOEt-CH2Cl2 1-1)

Sources & evidence

ORD record
ord-2eabce25fa2847e9b485eebaff57f651
Source dataset
uspto-grants-2000_08
Patent number
US06100404

Reaction notes

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