Sodium hydride → HCID 15672493, compound

Temperature

0 °C

In this example 42 g of 3-trifluoromethylbenylacetic acid in 100 ml of tetrahydrofuran was added to a cooled slurry containing 9.65 g of sodium hydride in 50 ml of tetrahydrofuran. The resulting mixture was allowed to stand for about 15-18 hours at room temperature, under a nitrogen atmosphere. The mixture was cooled to 0° C. and then 201 ml of a 1 molar solution of lithium bis[trimethylsilyl]amide in tetrahydrofuran was added. This mixture was stirred for 20 minutes at 0° C. and then 20.4 g of (α-ethoxycarbonylbenzyl)acetonitrile in 50 ml of tetrahydrofuran was added. The mixture was stirred and allowed to warm toward room temperature for 11/2 hours, and then added to 1,200 ml of water at room temperature. The aqueous mixture was extracted twice with petroleum ether. The extracts were combined and concentrated under vacuum, to a white paste. The solids were collected by suction filtration and dissolved in methylene chloride. The solution was washed once with aqueous 10% hydrochloric acid; twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated yielding 17.2 g of the title compound as a white solid. 2.2 g of this solid was further purified by recrystallization from methanol, MP 111° to 112° C.

1. stirringThe mixture was stirred
2. temperatureto warm toward room temperature for 11/2 hours
3. extractionThe aqueous mixture was extracted twice with petroleum ether
4. concentrationconcentrated under vacuum, to a white paste
5. filtrationThe solids were collected by suction filtration
6. dissolutiondissolved in methylene chloride
7. washThe solution was washed once with aqueous 10% hydrochloric acid
8. dry with materialtwice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate
9. customevaporated

ORD record

ord-89fe4d14c180487d94a2f4c00d362086

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04978386