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Ethyl Acetate → 1-(4-Ethyl-1,3-thiazol-2-yl)acetone

HRID 1951536
Notes
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Reaction equation

HRID 1951536 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1)[CH3:2].C([Li])CCC.[C:14](OCC)(=[O:16])[CH3:15]>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:8][C:14]([CH3:15])=[O:16])[S:6][CH:7]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5205684-Ethyl-2-methylthiazoleHCID 178418339Butyllithium

Product 1

HCID 594923381-(4-Ethyl-1,3-thiazol-2-yl)acetone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.70 g (13.4 mmol) of the compound from example 16A are dissolved in 15 ml of abs. THF and, at −78° C., 5.88 ml (14.7 mmol) of n-butyllithium (2.5 M solution in hexane) are added dropwise. After stirring at −78° C. for 2 hours, 2.00 g (22.7 mmol) of ethyl acetate are added as a solution in 10 ml of abs. THF. The mixture is stirred at −78° C. for 1 h and then warmed to room temperature. It is then hydrolyzed with sodium bicarbonate solution, and the mixture is extracted three times with diethyl ether. The combined organic phases are dried with magnesium sulfate, and the solvent is removed in a rotary evaporator. 1.89 g (84% of theory) of the title compound are obtained. GC-MS (Method 2): Rt=4.20 min; MS (Elpos): m/z=169 [M]+.

Workup

  1. stirringThe mixture is stirred at −78° C. for 1 h
  2. temperaturewarmed to room temperature
  3. extractionhydrolyzed with sodium bicarbonate solution, and the mixture is extracted three times with diethyl ether
  4. dry with materialThe combined organic phases are dried with magnesium sulfate
  5. customthe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-143db9d6ee124b54822d8b658be4f104
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404723B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes