Aluminium lithium hydride → HCID 2726702, compound

Temperature

25 °C

To an ice-cold suspension of LAH (0.056 g, 1.40 mmol) the 8 ml of anhydrous THF was added dropwise a solution of 4-(4-Trifluoromethyl-phenyl)-thiazole-2-carboxylic acid ethyl ester (0.21 g, 0.71 mmol) in the 5 ml of THF. The reaction mixture was stirred at 25° C. for 1 h. After the completion of the reaction mixture (TLC monitoring), cooled the reaction mixture to 0° C. and quenched with 2.5 ml of water followed by the addition of 15% NaOH solution (2 mL) and finally 4 ml of water. The resulting solution was filtered through celite bed and the filtrate was concentrated under reduced pressure. Water (50 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to give the desired product (0.13 g, 70%). The other derivatives were also prepared by the same general method.

1. temperatureAfter the completion of the reaction mixture (TLC monitoring), cooled the reaction mixture to 0° C.
2. customquenched with 2.5 ml of water
3. additionfollowed by the addition of 15% NaOH solution (2 mL) and finally 4 ml of water
4. filtrationThe resulting solution was filtered through celite bed
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionWater (50 mL) was added
7. extractionextracted with ethyl acetate (3×50 mL)
8. washThe combined organics was washed with water, brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-662c07f4cb9549129ec0d843faaeaf84

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088791B2