1,2-Dimethoxyethane → HCID 131718398, compound

Temperature

-70 °C

To a 3-neck flask equipped with a dropping funnel, a thermometer, and a condenser with a drying tube were added 5 grams of 2-chloro-4-trifluoromethyl pyridine and 5 ml of ethylene glycol dimethyl ether. The mixture was cooled to -70° C. and 22 ml of LDA were slowly added with the temperature maintained below -55° C. The reaction mixture was stirred at -70° C. for 1.5 hours, and 3.5 ml of 2-trifluoromethyl benzaldehyde added. The reaction mixture was stirred in a dry-ice bath, then at room temperature over night. Fifteen ml of saturated aqueous ammonium chloride solution was added, the solvent stripped and the oil residue washed with water and extracted with methylene chloride (3 times). The combined methylene chloride layers were washed with brine, dried and stripped to yield a brown oil. The brown oil was put onto a silica gel column and eluted with a 1:1 mixture of hexane and diethyl ether to yield 6.2 grams of 2-chloro-3-(1-hydroxy-2'-trifluoromethyl-benzyl)-4-trifluoro methyl-pyridine.

1. customTo a 3-neck flask equipped with a dropping funnel
2. temperaturemaintained below -55° C
3. stirringThe reaction mixture was stirred in a dry-ice bath
4. waitat room temperature over night
5. washthe oil residue washed with water
6. extractionextracted with methylene chloride (3 times)
7. washThe combined methylene chloride layers were washed with brine
8. customdried
9. customto yield a brown oil
10. washeluted with a 1:1 mixture of hexane and diethyl ether

ORD record

ord-7da0af74090d499c84f956c0e86ad187

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05585327