Sodium Bicarbonate → 1-(2,4-Dimethyl-5-thiazolyl)-1-(3-pyridyl)ethanol

HRID 975065Notes

Reaction equation

HRID 975065 reaction equation
[C:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].[Li][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])O.[Na+]>C(OCC)C>[CH3:9][C:7]1[S:8][C:4]([C:1]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([OH:3])[CH3:2])=[C:5]([CH3:10])[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5208882,4-Dimethyl-5-acetylthiazoleHCID 178418470HCID 178418470, compound

Product 1

HCID 189363201-(2,4-Dimethyl-5-thiazolyl)-1-(3-pyridyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-Acetyl-2,4-dimethylthiazole (2.5 g) in dry diethylether (10 ml) was added dropwise to a stirred solution of 3-lithiopyridine (from 3.5 g 3-bromopyridine) in diethylether at -70° C. After 3 hours the mixture was allowed to warm to room temperature. After a further 1 hour, aqueous sodium hydrogen carbonate was added and the organic layer was separated. The aqueous layer was extracted with diethylether. The material obtained from the combined organic layers was purified by flash chromatography to give the title compound, m.p. 107.5°-109° C.

Workup

  1. waitAfter a further 1 hour
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethylether
  4. customThe material obtained from the combined organic layers
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f3405ff8c28d4a65bdc0233cb155eb45
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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