반응 #504982

반응 방정식

Glucosamine hydrochloride

2-acetyl-dimedone

→

crude product

수율 188.5%

2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranose

수율 188.5%

용매

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred
2. 2
   온도under reflux for 2.5 hours
3. 3
   온도the reaction mixture was cooled to room temperature
4. 4
   여과filtered
5. 5
   기타The filtrate was evaporated
6. 6
   세척the resulting solid residue was washed on a funnel with ether (3×500 mL)
7. 7
   기타dried

실험 절차

Glucosamine hydrochloride (50 g, 231 mmol) was suspended in anhydrous methanol (500 mL), then 2-acetyl-dimedone sodium salt (47.3 g, 231 mmol) was added. The reaction mixture was stirred at room temperature for 10 minutes, then 2-acetyl-dimedone (21.1 g, 115.9 mmol) was added. The reaction mixture was stirred under reflux for 2.5 hours and monitored by tlc. At the completion of the reaction (TLC: MeCN—H20, 10:2), the reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated and the resulting solid residue was washed on a funnel with ether (3×500 mL) and dried to give crude product (75 g, 94%). No further purification was required for the next reaction.

출처