Acetic Anhydride → HCID 13050869, compound

HRID 371302Notes

Reaction equation

HRID 371302 reaction equation
[OH:1][C:2]1[C:23]2[C:22](=[O:24])[C:9]3[O:10][C:11](=[O:21])[C:12]4[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([O:19][CH3:20])[C:13]=4[C:8]=3[C:7](=[O:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[C:26]([O:1][C:2]1[C:23]2[C:22](=[O:24])[C:9]3[O:10][C:11](=[O:21])[C:12]4[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([O:19][CH3:20])[C:13]=4[C:8]=3[C:7](=[O:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 156387WS-5995 A

Product 1

HCID 13050869HCID 13050869, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In pyridine (10 ml) was dissolved 8-hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-5,7,12-trione (150 mg) as obtained in Example 15, followed by addition of acetic anhydride (5 ml). The mixture was allowed to stand overnight. The solvent was then distilled off under reduced pressure and the residue was extracted with chloroform. The solvent layer was washed with dilute HCl and water, and dried over sodium sulfate. The solvent was distilled off and the residue was crystallized from diethyl ether to give crystals (45 mg) of 8-acetoxy-1-methoxy-3-methyl-7,12-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-5,7,12-trione.

Workup

  1. customas obtained in Example 15
  2. distillationThe solvent was then distilled off under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. washThe solvent layer was washed with dilute HCl and water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-7bb8553c8c724826858d55ba63158a88
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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