반응 #955979

반응 방정식

hydrazone alcohol

1-(5-Hydroxy-3-methyl-penta-1,3-dienyl)-4-(2-methoxymethyl-pyrrolidin-1-ylimino)-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-ol

→

hydrazone aldehyde

수율 80.7%

5-[1-Hydroxy-4-(2-methoxymethyl-pyrrolidin-1-ylimino)-2,2-dimethyl-1,2,3,4-tetrahydro-naphthalen-1-yl]-3-methyl-penta-2,4-dienal

수율 80.7%

용매

acetone

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered over a bed of Celite®
2. 2
   세척washed with acetone
3. 3
   기타The combined filtrates and washings were evaporated
4. 4
   기타to give a residue, which
5. 5
   기타was purified by column chromatography on silica using 30% ethyl acetate-hexane

실험 절차

A mixture of hydrazone alcohol [29] (69 mg, 0.17 mmol) and MnO2 (300.8 mg, 3.46 mmol) in acetone (5 mL) was stirred at RT for 16 hr. The reaction mixture was filtered over a bed of Celite® and washed with acetone. The combined filtrates and washings were evaporated to give a residue, which was purified by column chromatography on silica using 30% ethyl acetate-hexane to provide the hydrazone aldehyde [30] (54.4 mg, 79%) and [α]D−532.6 (c 0.43, CH2Cl2).

출처