Lithium Carbonate → 9-Benzyl-6-methoxy-9H-carbazol-4-ol

온도

80 °C

To a mixture of 9-benzyl-6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (4.23 g, 13.85 mmol) in ethylene glycol: p-dioxane ((1:1) 150 mL) is added copper (II) chloride (9.31 g, 69.26 mmol). The mixture is heated at 80° C. for 30 minutes. The mixture is partitioned between water and Et2O. The layers are separated and the organic layer washed with water (100 mL). The ether layer is dried over anhydrous sodium sulfate, filtered and concentrated. The residue is dissolved in DMF (50 mL) to which is added lithium bromide (2.45 g, 28.3 mmol) and lithium carbonate (2.09 g, 28.3 mnmol). The mixture is heated at 120° C. for 5 h. The mixture is partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with water (200 mL). Column chromatography (250 mL) silica gel using ethyl acetate/ hexanes (20/80) gave 2.5 g (73%) of the title compound; IR (drift) 3471, 1482, 1469, 1450, 1328, 1198, 1171, 1144, 805, 799, 780, 745, 724, 717, 701 cm−1. 1H NMR (DMSO-d6) δ3.82, 5.54, 6.56, 6.97), 7.14, 7.23, 7.43, 7.72; Anal. Calcd for C20H17NO2: C, 79.18; H, 5.65; N, 4.62. Found: C, 78.99; H, 5.75; N, 4.63.

1. customThe mixture is partitioned between water and Et2O
2. customThe layers are separated
3. washthe organic layer washed with water (100 mL)
4. dry with materialThe ether layer is dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. dissolutionThe residue is dissolved in DMF (50 mL) to which
8. temperatureThe mixture is heated at 120° C. for 5 h
9. customThe mixture is partitioned between water and ethyl acetate
10. customThe layers are separated
11. washthe organic layer washed twice with water (200 mL)

ORD 기록

ord-ac4d131f7c31461d881ca44338bdbbf2

출처 데이터셋

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06514968B1