Thiazole → 1-(1,3-Thiazol-2-yl)cyclobutan-1-ol

HRID 2362615Notes

Reaction equation

HRID 2362615 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[C:11]1(=[O:15])[CH2:14][CH2:13][CH2:12]1>O1CCCC1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:11]1([OH:15])[CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 14496CyclobutanoneHCID 178418339Butyllithium

Product 1

HCID 129928101-(1,3-Thiazol-2-yl)cyclobutan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (−78° C.) solution of thiazole (6.59 ml, 93 mmol) in tetrahydrofuran (238 mL) was added n-butyllithium (58.0 mL, 93 mmol) dropwise. The reaction was stirred for 15 minutes, and cyclobutanone (5.0 g, 71.3 mmol) was added via syringe. The reaction was stirred for 10 minutes and was then quenched by the addition of saturated aqueous bicarbonate solution. The cold bath was removed, and the reaction was warmed to room temperature. Ethyl acetate was added, and the layers were separated. The aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the subsequent step without further purification. MS ESI(+) m/z 156 [M+H]+.

Workup

  1. stirringThe reaction was stirred for 10 minutes
  2. customwas then quenched by the addition of saturated aqueous bicarbonate solution
  3. customThe cold bath was removed
  4. additionEthyl acetate was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with additional ethyl acetate (2×)
  7. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1c45f83c4d24fd0850a6c07e8e907c0
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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