Acetic Anhydride → HCID 19775905, compound

HRID 1613477Notes

Reaction equation

HRID 1613477 reaction equation
[OH:1][CH2:2][C:3]1([CH3:24])[CH:16]2[C:7]([CH3:22])([C:8]3[C:9](=[O:21])[CH:10]=[C:11]([CH:18]([CH3:20])[CH3:19])[C:12](=[O:17])[C:13]=3[CH2:14][CH2:15]2)[CH2:6][CH2:5][C:4]1=[O:23].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:25]([O:1][CH2:2][C:3]1([CH3:24])[CH:16]2[C:7]([CH3:22])([C:8]3[C:9](=[O:21])[CH:10]=[C:11]([CH:18]([CH3:20])[CH3:19])[C:12](=[O:17])[C:13]=3[CH2:14][CH2:15]2)[CH2:6][CH2:5][C:4]1=[O:23])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19775902HCID 19775902, compound

Product 1

HCID 19775905HCID 19775905, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture consisting of 60 mg of the 5,6,8,8a,9,10-hexahydro-8-hydroxymethyl-4b,8-dimethyl-2-(1-methylethyl)-1,4,7(4bH)-phenanthrenetrione obtained in Example 2, 0.1 ml of acetic anhydride and 1 ml of pyridine was stirred at room temperature for 2.5 hours. The reaction mixture was poured into ice water, and extracted with ether. The organic layer was washed with an aqueous saturated with sodium chloride, dried with anhydrous magnesium sulfate, and concentrated. The resulting crude product was purified by a silica gel column chromatography (eluant: ether/n-hexane=1/2) to obtain 41 mg of 8-(acetoxymethyl)-5,6,8,8a,9,10-hexahydro-4b,8-dimethyl-2-(1-methylethyl)-1,4,7(4bH)-phenanthrenetrione.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with an aqueous saturated with sodium chloride
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product was purified by a silica gel column chromatography (eluant: ether/n-hexane=1/2)

Sources & evidence

ORD record
ord-250b17598a9d4ac2af9ba68cb5e4cce5
Source dataset
uspto-grants-1993_03
Patent number
US05192817

Reaction notes

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