Hydrochloric Acid → HCID 131721447, compound

Lithium aluminium hydride (0.76 g, 20.03 mmol) was added in small portions to a stirred tetrahydrofuran (200 ml) solution of 4-(4-acetoxyphenyl)-7-methoxy-3-(4-(trifluoromethyl)phenyl)-coumarin (4.54 g, 9.99 mmol). After complete addition, the mixture was stirred at room temperature for 30 min., then treated dropwise with 6M hydrochloric acid (30 ml). The resulting mixture was heated to 60-65° C. for 3 h, cooled and diluted with water (100 ml) and ethyl acetate (50 ml). The aqueous layer was separated and further extracted with ethyl acetate (3×100 ml). The combined organic solutions were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated to give an orange solid. This was recrystallised from ethanol/water (65 ml, 10:3) to give the first crop of solid product as colourless needles. The mother liquors were evaporated to give an orange gum, which was subjected to a second aqueous ethanol recrystallisation to give a second crop of colourless needles. The solids were combined and vacuum dried.

1. additionAfter complete addition
2. temperatureThe resulting mixture was heated to 60-65° C. for 3 h
3. temperaturecooled
4. customThe aqueous layer was separated
5. extractionfurther extracted with ethyl acetate (3×100 ml)
6. washThe combined organic solutions were washed with saturated aqueous sodium chloride
7. dry with materialdried over sodium sulfate
8. customevaporated
9. customto give an orange solid
10. customThis was recrystallised from ethanol/water (65 ml, 10:3)
11. customto give the first crop of solid product as colourless needles
12. customThe mother liquors were evaporated
13. customto give an orange gum, which
14. customwas subjected to a second aqueous ethanol recrystallisation
15. customto give a second crop of colourless needles
16. customvacuum dried

ORD record

ord-fc68e415846d4c4eaed9e011f88aebec

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06316494B1