Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate → (2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

To a mixture of 2.6 g (0.01 mol) of ethyl 2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylate and 10 ml of ethanol was added 0.62 g of sodium cyanoborohydride. The reaction mixture was stirred for 5 minutes and 0.40 g of sodium borohydride was added. The temperature of the reaction mixture raised spontaneously to boiling point. The reaction mixture was stirred for 30 minutes and quenched with water. The aqueous mixture was extracted with ether. The ether solution was dried over CaSO4 and concentrated under reduced pressure. The residue was crystallized from petroleum ether to give 1.6 g (74%) of 2-chloro-4-(trifluoromethyl)-5-thiazolemethanol, mp 39°-45° C.

1. temperatureThe temperature of the reaction mixture raised spontaneously
2. stirringThe reaction mixture was stirred for 30 minutes
3. customquenched with water
4. extractionThe aqueous mixture was extracted with ether
5. dry with materialThe ether solution was dried over CaSO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was crystallized from petroleum ether

ORD record

ord-8334457da34d47aaaf42e126740c07d6

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04377693