Réaction #11253

Équation de réaction

benzyl alcohol

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

phosphorous oxychloride

ethyl acetate

phosphorous oxychloride

→

dibenzyl phosphate

Rendement 32.0%

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

Rendement 32.0%

Solvants

pyridine

hydrochloric acid

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source