Реакция #11253

Уравнение реакции

benzyl alcohol

9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

phosphorous oxychloride

ethyl acetate

phosphorous oxychloride

→

dibenzyl phosphate

Выход 32.0%

Dibenzyl 1,3-dioxo-4-phenyl-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-yl phosphate

Выход 32.0%

Растворители

pyridine

hydrochloric acid

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   ДругоеThe organic phase was dried
3. 3
   Другоеthe drying agent was removed
4. 4
   Концентрированиеthe solution was concentrated to dryness
5. 5
   Другоеbefore being chromatographed on silica eluting with methanol/dichloromethane (3:97)

Методика

To a solution of 9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (I; Ar=phenyl) (0.50 g, 1.52 mmol) in pyridine (30 mL) under nitrogen was added phosphorous oxychloride (140 □L, 1.52 mmol) dropwise. After 40 minutes stirring at room temperature a further portion of phosphorous oxychloride (40 □L) was added and then after another 20 minutes, benzyl alcohol (0.66 mL, 6.38 mmol) was added. After 3 hours the reaction mixture was diluted with 1N hydrochloric acid and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness, before being chromatographed on silica eluting with methanol/dichloromethane (3:97) to give the dibenzyl phosphate (336) (284 mg, 32%) as a pale yellow powder, mp 193–194° C. 1H NMR δ [(CD3)2SO] 12.12 (br s, 1H), 11.15 (br s, 1H), 8.81 (br s, 1H), 7.69 (s, 1H), 7.63 (m, 3H), 7.48–7.34 (m, 14H), 5.22 (d, JH-F=8.3 Hz, 4H). Found: C, 69.65; H, 4.37; N, 4.88; P, 5.26. C34H25N2O6P requires: C, 69.38; H, 4.28; N, 4.76; P, 5.26.

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