Water → 1-[2-(5-Bromo-4,6-dioxo-2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-2-(benzoyl)pyrrole

HRID 53905Notes

Reaction equation

HRID 53905 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[Na].[O:11]=[C:12]1[CH:17]([CH2:18][CH2:19][N:20]2[CH:24]=[CH:23][CH:22]=[C:21]2[C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16](=[O:33])[O:15][C:14]([CH3:35])([CH3:34])[O:13]1.O>O1CCCC1>[Br:7][C:17]1([CH2:18][CH2:19][N:20]2[CH:24]=[CH:23][CH:22]=[C:21]2[C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12](=[O:11])[O:13][C:14]([CH3:35])([CH3:34])[O:15][C:16]1=[O:33]

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 109147952-Benzoyl-1-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]pyrrole

Product 1

HCID 109386931-[2-(5-Bromo-4,6-dioxo-2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-2-(benzoyl)pyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridinium bromide perbromide (11.51 g, 36 mmoles) in tetrahydrofuran (25 ml) was added dropwise at 0°-5° C. to a vigorously stirred suspension of the sodium salt of 1-[2-(4,6-dioxo-2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-2-benzoylpyrrole (VI, prepared as described above, 13.5 g, 37.2 mole). The mixture was stirred for 1 hour at 0°-5° C. The mixture was then poured into water (600 ml) and extracted three times with diethyl ether (100 ml, then 2×50 ml). The organic phase was separated and washed with two 200 ml portions of water, dried over magnesium sulfate and evaporated to afford crystalline 1-[2-(5-bromo-4,6-dioxo-2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-2-(benzoyl)pyrrole (VIIa). The product could be recrystallized from ethyl acetate/hexane to give material with the following properties: m.p. 89°-91° C. 1H NMR (CDCl3): delta 1.81 (s, 3H); 2.00 (s, 3H); 3.19 (t, 2H); 4.58 (t, 2H); 6.19 (dd, 1H); 6.71 (dd, 1H); 6.89 (dd, 1H); 7.4-7.55 (m, 3H); 7.78 (dd, 2H). 13C NMR (CDCl3): delta 26.8, 28.9, 39.7, 43.5, 45.8, 107.3, 123.5, 127.9, 129.2, 130.3, 131.4, 139.1, 163.0, 186.9.

Workup

  1. extractionextracted three times with diethyl ether (100 ml
  2. customThe organic phase was separated
  3. washwashed with two 200 ml portions of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d9960f19cab04676a3c419954660e2d3
Source dataset
uspto-grants-1997_04
Patent number
US05621115

Reaction notes

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