Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → 4-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

HRID 2396648Notes

Reaction equation

HRID 2396648 reaction equation
[CH2:1]([C:4]1[C:5]([O:17][Si](C(C)(C)C)(C)C)=[C:6]2[C:10](=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14])[CH2:9][O:8][C:7]2=[O:16])[CH:2]=[CH2:3].[CH3:25][C:26](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:27]>C(O)(=O)C>[C:26]([O:17][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[C:12]([O:13][CH3:14])[C:11]([CH3:15])=[C:10]2[C:6]=1[C:7](=[O:16])[O:8][CH2:9]2)(=[O:27])[CH3:25]

Participants

4

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 100663665-Allyl-4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

Product 1

HCID 190463174-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-allyl-4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran [(J. W. Patterson and G. Huang, Chemical Communications, 1579 (1991)](7.5 g) in acetic acid (95 ml) and acetic arthydride (95 ml) was refluxed for 18 hours, then cooled and poured into ice water. The solution was extracted with ethyl acetate, and the extract washed with dilute aqueous sodium bicarbonate, followed by water, then dried and evaporated. The residue was chromatographed on silica gel, eluting with 7:3 hexane:ethyl acetate, to give 4-acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran, mp 101°-102° C.

Workup

  1. temperaturecooled
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe extract washed with dilute aqueous sodium bicarbonate
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 7:3 hexane

Sources & evidence

ORD record
ord-4db50147fc27408585c519278027dbac
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

Loading…