Diethyl Ether → HCID 57182367, compound

HRID 1613476Notes

Reaction equation

HRID 1613476 reaction equation
[CH3:1][C:2]1[CH:15]2[C:6]([CH3:21])([C:7]3[C:8](=[O:20])[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11](=[O:16])[C:12]=3[CH2:13][CH2:14]2)[CH2:5][CH2:4][C:3]=1[C:22]([OH:24])=[O:23].[CH3:25]COCC>>[CH3:1][C:2]1[CH:15]2[C:6]([CH3:21])([C:7]3[C:8](=[O:20])[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11](=[O:16])[C:12]=3[CH2:13][CH2:14]2)[CH2:5][CH2:4][C:3]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 383736HCID 383736, compound

Product 1

HCID 57182367HCID 57182367, compound

Procedure

63 Milligrams of the 3,4,4a,5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylic acid obtained in Example 1 was dissolved in 8 ml of ether, then under ice-cooling condition, a diazomethane-ether solution was added thereto and the mixture was stirred for 30 minutes. Ether was removed by distillation. The resulting crude product was purified by a silica gel column chromatography (eluant: ether/n-hexane=1/2) to obtain 8.8 mg of methyl 3,4,4a, 5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylate.

Workup

  1. temperatureunder ice-cooling condition
  2. customEther was removed by distillation
  3. customThe resulting crude product was purified by a silica gel column chromatography (eluant: ether/n-hexane=1/2)

Sources & evidence

ORD record
ord-3e47b28d42904f3fb8e70118b42de436
Source dataset
uspto-grants-1993_03
Patent number
US05192817

Reaction notes

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