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

HRID 860622Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:7][C:8]=1[C:9]([CH3:13])=[CH:10][O:11]C)([CH3:3])[CH3:2].Cl>O1CCCC1>[CH:1]([C:4]1[N:5]=[C:6]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)[S:7][C:8]=1[CH:9]([CH3:13])[CH:10]=[O:11])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Isopropyl-5-(2-methoxy-1-methyl-vinyl)-2-(4-trifluoromethyl-phenyl)-thiazole is dissolved into anhydrous tetrahydrofuran (100 mL) and concentrated hydrochloric acid (5 mL) is added with stirring under nitrogen. The reaction is heated to 50° C. and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully neutralized with sodium hydroxide, extracted with diethyl ether, washed, dried, and concentrated. The 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionaldehyde (4.6 g, 14.05 mmol), 82% two steps, is obtained in pure form after flash column chromatography.

Workup

additionis added
customUpon complete consumption of starting material
extractionextracted with diethyl ether
washwashed
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-e38be429fc55431cb05cde3f03d0a22a
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153878B2

Reaction notes

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