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

HRID 2396648ノート

反応式

HRID 2396648 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4db50147fc27408585c519278027dbac
出典データセット
uspto-grants-1996_02
特許番号
US05493030

反応ノート

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