Réaction #955979

Équation de réaction

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

Rendement 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

Rendement 80.7%

Solvants

acetone

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source