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

HRID 860615Notes

Reaction equation

HRID 860615 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-3d5ff2c70148464db69f32f16720c68c
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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