Cyclohexanone → 12,14-Dihydroxy-3-oxocard-20(22)-enolide
Reaction equation
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][C@@H:13]([OH:27])[C@:14]4([CH3:26])[C@@H:18]([C:19]5[CH2:24][O:23][C:21](=[O:22])[CH:20]=5)[CH2:17][CH2:16][C@:15]4([OH:25])[C@@H:10]3[CH2:9][CH2:8][C@@H:7]1[CH2:6][C@@H:5]([OH:28])[CH2:4][CH2:3]2.C1(=O)CCCCC1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(C)C=CC=CC=1>[CH3:1][C@@:2]12[CH:11]3[CH2:12][C@@H:13]([OH:27])[C@:14]4([CH3:26])[C@@H:18]([C:19]5[CH2:24][O:23][C:21](=[O:22])[CH:20]=5)[CH2:17][CH2:16][C@:15]4([OH:25])[CH:10]3[CH2:9][CH2:8][C@@H:7]1[CH2:6][C:5](=[O:28])[CH2:4][CH2:3]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 488 mg digoxigenin, 7.5 ml toluene, 3.75 ml cyclohexanone, and 550 mg aluminum isopropoxide was heated under reflux for 2.3 hours and then concentrated in vacuo to half of its original volume. Two hundred μl water was added and the mixture was evaporated in vacuo to dryness. The powdery solid was dried in vacuo over overnight. The dry residue was stirred in 25 ml methanol and the resulting mixture was filtered. The residue on the funnel was washed with 25 ml methanol. The filtrate and washing were combined and evaporated in vacuo affording 920 mg white solid.
Workup
- temperaturewas heated
- temperatureunder reflux for 2.3 hours
- concentrationconcentrated in vacuo to half of its original volume
- additionTwo hundred μl water was added
- customthe mixture was evaporated in vacuo to dryness
- customThe powdery solid was dried in vacuo over overnight
- filtrationthe resulting mixture was filtered
- washThe residue on the funnel was washed with 25 ml methanol
- washThe filtrate and washing
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-45f584bdff344b7bbc064a5fde065ad2
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05846703
Reaction notes
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