Diethyl Ether → HCID 86751263, compound

Temperature

-75 °C

To a suspension of 7.0 g of 5-bromopyrimidine in 150 ml of diethyl ether at -75° C., 20 ml of 2.5M butyl lithium in hexane were added while keeping the temperature below -50° C. The reaction mixture was then stirred at -75° C. for 1.5 hours. 7.66 g of 2-trifluoromethylbenzaldehyde were added while keeping the temperature below -50° C. and the reaction mixture was then stirred at -75° C. for one hour. The reaction mixture was then quenched with water. The resulting layers were separated. The aqueous layer was extracted again with diethyl ether. The combined organic layers were dried (MgSO4), filtered and concentrated to a yellow oil which turned orange upon standing overnight. Purification by column chromatography (silica gel), eluted first with a 1:1 mixture of hexane and diethyl ether, and then with diethyl ether, to yield 0.13 g of 5-(1-hydroxy-2,-trifluoromethylbenzyl)pyrimidine.

1. customthe temperature below -50° C
2. customthe temperature below -50° C.
3. stirringthe reaction mixture was then stirred at -75° C. for one hour
4. customThe reaction mixture was then quenched with water
5. customThe resulting layers were separated
6. extractionThe aqueous layer was extracted again with diethyl ether
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated to a yellow oil which
10. waitupon standing overnight
11. customPurification by column chromatography (silica gel)
12. washeluted first with a 1:1 mixture of hexane and diethyl ether

ORD record

ord-68ace709de524820a8c4d886da98cde7

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05672567