Thiazole → HCID 22716763, compound

HRID 2187898Notes

Reaction equation

HRID 2187898 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[CH3:11][S:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>C1COCC1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:17]([C:16]1[CH:19]=[CH:20][C:13]([S:12][CH3:11])=[CH:14][CH:15]=1)[OH:18]

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 769854-(Methylthio)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 22716763HCID 22716763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of thiazole (5.0 g, 58.7 mmol) in THF (250 ml) was added n-butyllithium (2.5M in hexanes, 23.5 ml, 58.7 mmol) dropwise and the resulting solution was stirred at −78° C. for 10 min. 4-(Methylthio)benzaldehyde (7.1 ml, 53.4 mmol) was then added at −78° C. The resulting mixture was stirred until completion, and quenched with a saturated aqueous solution of NH4Cl. The mixture was then diluted with EtOAc and HCl 10%, extracted and washed (NaHCO3 (sat.), brine). The organic phase was dried over MgSO4 and concentrated. The residue was then purified by flash chromatography (80% CH2Cl2/20% EtOAc) to yield (1,3-Thiazol-2-yl)[4-(methylthio)phenyl]methanol.

Workup

  1. stirringThe resulting mixture was stirred until completion
  2. customquenched with a saturated aqueous solution of NH4Cl
  3. additionThe mixture was then diluted with EtOAc and HCl 10%
  4. extractionextracted
  5. washwashed (NaHCO3 (sat.), brine)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was then purified by flash chromatography (80% CH2Cl2/20% EtOAc)

Sources & evidence

ORD record
ord-2b6d8b44fefc4fbc9e9c7161db384a32
Source dataset
uspto-grants-2002_06
Patent number
US06410563B1

Reaction notes

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