Phthalide → Indeno(1,2-c)isochromene-5,11-dione

HRID 555330노트

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HRID 555330 반응식
C[O-].[Na+].[C:4]([C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10])([OH:6])=O.[C:15]1([C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]O1)=[O:16]>C(OCC)(=O)C>[CH:20]1[C:19]2[C:18]3[C:9](=[O:10])[C:8]4[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=4[C:4]=3[O:6][C:15](=[O:16])[C:24]=2[CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 6885PhthalideHCID 8406Phthalaldehydic acidHCID 10942334Sodium Methoxide

생성물 1

HCID 265728Indeno(1,2-c)isochromene-5,11-dione수율 86%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

Sodium methoxide (40 mL of a 4 M methanolic solution) was added to a solution of 2-carboxybenzaldehyde 1d (1.000 g, 7.455 mmol) and phthalide 2d (1.119 g, 7.455 mmol) in ethyl acetate (20 mL). The solution was heated at 65° C. for 18 h, concentrated, and acidified with concd HCl. The resulting mixture was diluted with benzene (125 mL), TsOH (100 mg) was added, and the solution was heated for 7 h at reflux in a flask affixed with a Dean-Stark trap. The solution was cooled to room temperature, concentrated, diluted with CHCl3 (150 mL), and washed with sat NaHCO3 (3×50 mL) and sat NaCl (50 mL). The organic layer was dried over sodium sulfate and concentrated to provide indenobenzopyran 4d as an orange solid (1.583 g, 86%): mp 258-259° C. (published mp 257° C.). 1H NMR (CDCl3) δ 8.40 (d, J=8.56 Hz, 1 H), 8.32 (d, J=7.93 Hz, 1H), 7.84-7.79 (m, 1 H), 7.61-7.39 (m, 5 H). Additional details regarding the synthesis of compound 8 are found in Pailer et al., Monatsh Chem., 92:1037-47 (1961), the synthetic disclosure of which is incorporated herein by reference.

후처리

  1. concentrationconcentrated
  2. additionThe resulting mixture was diluted with benzene (125 mL), TsOH (100 mg)
  3. additionwas added
  4. temperaturethe solution was heated for 7 h
  5. temperatureat reflux in a flask
  6. temperatureThe solution was cooled to room temperature
  7. concentrationconcentrated
  8. additiondiluted with CHCl3 (150 mL)
  9. washwashed
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-73f4bc11d40245cb89c7413875ced5f8
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053443B2

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