반응 #160019

반응 방정식

Sodium methoxide

2-carboxybenzaldehyde

phthalide

→

indenobenzopyran

수율 86.0%

Benz[d]indeno[1,2-b]pyran-5,11-dione

수율 86.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   농축concentrated
2. 2
   workup.ADDITIONThe resulting mixture was diluted with benzene (125 mL), TsOH (100 mg)
3. 3
   workup.ADDITIONwas added
4. 4
   온도the solution was heated for 7 h
5. 5
   온도at reflux in a flask
6. 6
   온도The solution was cooled to room temperature
7. 7
   농축concentrated
8. 8
   workup.ADDITIONdiluted with CHCl3 (150 mL)
9. 9
   세척washed
10. 10
    건조The organic layer was dried over sodium sulfate
11. 11
    농축concentrated

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 coned 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, 1H), 8.32 (d, J=7.93 Hz, 1H), 7.84-7.79 (m, 1H), 7.61-7.39 (m, 5H). 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.

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