1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 6-methoxybenzofuran-2-carboxylate

HRID 1054

反応式

HRID 1054 の反応式
[CH:1]([C:3]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=O.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:3]2[CH:1]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[O:5][C:4]=2[CH:11]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19364036Methyl 2-formyl-5-methoxyphenoxyacetate

生成物 1

HCID 3016964Methyl 6-methoxybenzofuran-2-carboxylate収率 57%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of methyl 2-formyl-5-methoxyphenoxyacetate (27.7 g), 1,8-diazabicyclo[5.4.0]-7-undecene (40.8 g) and toluene (200 ml) was heated under refluxing conditions for 4 hours. The reaction mixture was concentrated under reduced pressure; after 6N hydrochloric acid was added, the residue was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; 10% hydrochloric acid-methanol (30 ml) was added to the residue, followed by heating at 70° to 80° C. for 4 hours. The reaction mixture was concentrated under reduced pressure; water was added, followed by extraction with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with chloroform-hexane (1:2, v/v), methyl 6-methoxybenzofuran-2-carboxylate (14.3 g, 57%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless prisms having a melting point of 97° to 98° C.

後処理

  1. temperaturewas heated under refluxing conditions for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionafter 6N hydrochloric acid was added
  4. extractionthe residue was extracted with ethyl acetate
  5. washAfter the ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off
  8. addition10% hydrochloric acid-methanol (30 ml) was added to the residue
  9. temperatureby heating at 70° to 80° C. for 4 hours
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. additionwater was added
  12. extractionfollowed by extraction with ethyl acetate
  13. washAfter the ethyl acetate layer was washed with water
  14. dry with materialdried (MgSO4)
  15. distillationthe solvent was distilled off
  16. washFrom the fraction eluted with chloroform-hexane (1:2

出典と根拠

ORDレコード
ord-4b3d1be49f204b63a88b6e40011ab757
出典データセット
uspto-grants-1998_03
特許番号
US05723479

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