Water → (2-(2-Chlorophenyl)thiazol-4-yl)methanol

To a solution of ethyl 2-(2-chlorophenyl)-4-thiazolecarboxylate (1.34 g, 5.0 mmol), prepared as described above, in CH2Cl2 (20 mL) at −78° C. is added diisobutylaluminum hydride (10.5 mL of 1.0 M solution in toluene, 10.5 mmol) and the resulting reaction mixture is stirred at −78° C. for 1 hour after which time sodium fluoride (1.5 g) and water (0.5 mL) are added and the reaction mixture is allowed to warm to room temperature and filtered. The filtrate is concentrated to provide the crude reduction product which is purified by column chromatography (10% ethyl acetate in hexanes) to afford 138 mg of [2-(2-chlorophenyl)-1,3-thiazol-4-yl]carboxyaldehyde and 605 mg of [2-(2-chlorophenyl)-1,3-thiazol-4-yl]methanol. The of [2-(2-chlorophenyl)-1,3-thiazol-4-yl]carboxyaldehyde portion is then used for subsequent steps while the [2-(2-chlorophenyl)-1,3-thiazol-4-yl]methanol portion is converted to [2-(2-chlorophenyl)-1,3-thiazol-4-yl]carboxyaldehyde via standard oxidation conditions.

1. customat −78° C.
2. customthe resulting reaction mixture
3. additionare added
4. filtrationfiltered
5. concentrationThe filtrate is concentrated
6. customto provide the crude reduction product which
7. customis purified by column chromatography (10% ethyl acetate in hexanes)

ORD record

ord-57c6598976154a6b9c6f5793fe031ea9

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07041690B2