Acetone → 2-Thiazol-2-yl-propan-2-ol

HRID 351750Notes

Reaction equation

HRID 351750 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[CH3:11][C:12]([CH3:14])=[O:13]>CCOCC>[OH:13][C:12]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([CH3:14])[CH3:11]

Participants

5

Procedure

To a solution of thiazole in ether (1 mL/mmol) at −78° C. was added 2.2M n-butyllithium in hexanes (1.1 eq) and the resulting mixture was stirred for 30 minutes. Acetone (1.2 eq) was added and the mixture was stirred at −78° C. for a further 30 minutes. The mixture was quenched in the cold with saturated aqueous ammonium chloride solution and warmed to room temperature, then partitioned between ether and water. The organic phase was dried and evaporated to yield the crude product as an orange-brown oil which was used as such in the next step.

Workup

  1. stirringthe mixture was stirred at −78° C. for a further 30 minutes
  2. customThe mixture was quenched in the cold with saturated aqueous ammonium chloride solution
  3. custompartitioned between ether and water
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-18753e767e0a4adeabc9d0493dff0b48
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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