Hydrochloric Acid → 2-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde

HRID 490737Notes

Reaction equation

HRID 490737 reaction equation
C[O:2][CH:3]=[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:21])[CH3:5].Cl>C1COCC1.C(OCC)(=O)C>[CH3:21][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:10][C:6]=1[CH:4]([CH3:5])[CH:3]=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 690570175-(2-Methoxy-1-methyl-vinyl)4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 587657492-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehydeYield 52.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(2-Methoxy-1-methyl-vinyl)-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (7.0 g, 22.3 mmol) in THF (200 mL) is treated with concentrated HCl aqueous solution (7 mL) at 50° C. for 2 hours. The reaction mixture is diluted with ethyl acetate, washed with sodium bicarbonate aqueous solution, dried over sodium sulfate. Concentration and column chromatography on silica gel provided the title compound (3.5 g).

Workup

  1. washwashed with sodium bicarbonate aqueous solution
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration and column chromatography on silica gel

Sources & evidence

ORD record
ord-b8643cec13104eeb8f04df415c0b20ac
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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