반응 #592594

반응 방정식

ammonia

diethylether

4-methyl-2-(trityl-amino)-picolinic acid methyl ester

compound B1

4-methyl-2-(trityl-amino)-picolinic acid methyl ester

diisobutylaluminium hydride

→

4-Methyl-2-(trityl-amino)-picolinaldehyde

용매

acetic acid

toluene acetone

toluene

toluene

반응 조건

후처리

1. 1
   여과The colorless precipitate is filtered off with suction
2. 2
   세척washed with toluene
3. 3
   추출The filtrate is extracted with brine
4. 4
   기타the organic phase is dried
5. 5
   농축concentrated to dryness
6. 6
   기타After purification of the crude product
7. 7
   기타on silica gel (eluent: toluene/ethyl acetate 20:1) and evaporation of the eluents, 0.438 g of the title compound
8. 8
   기타are obtained as a colorless, amorphous solid

실험 절차

A solution of 1.0 g of 4-methyl-2-(trityl-amino)-picolinic acid methyl ester (compound B1) in 35 ml of dry toluene is treated dropwise at −70° C. with 2.9 ml of a 1.5 M solution of diisobutylaluminium hydride in toluene. After 0.5 h 5 ml of diethylether and 2.9 ml of diluted aqueous acetic acid (20% strength) are added. After further 0.5 h the reaction mixture is warmed to room temperature and 29 ml of an aqueous solution of ammonia (25% strength) are added. The colorless precipitate is filtered off with suction and washed with toluene. The filtrate is extracted with brine, the organic phase is dried using sodium sulfate and concentrated to dryness. After purification of the crude product on silica gel (eluent: toluene/ethyl acetate 20:1) and evaporation of the eluents, 0.438 g of the title compound are obtained as a colorless, amorphous solid. M.p. 213° C. MS: 379.1 (MH+). TLC: Rf=0.66 (toluene/acetone 10:1).

출처