Acetic Anhydride → 7-Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid anhydride

HRID 1422079Notes

Reaction equation

HRID 1422079 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:14]([C:24]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[CH:30][CH:29]=4)=[C:25]([CH2:26][CH3:27])[C:12]3=[CH:11][CH:10]=1)=C(C(O)=O)C=2C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:42]([O:45][C:46](=[O:48])[CH3:47])(=[O:44])[CH3:43]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:17]2[N:13]3[C:14]([C:24]([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[CH:32][CH:33]=4)=[C:25]([CH2:26][CH3:27])[C:12]3=[CH:11][CH:10]=1)=[C:47]1[C:46](=[O:48])[O:45][C:42](=[O:44])[C:43]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 187069227Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid

Product 1

HCID 566372827-Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid anhydride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7Benzyloxy-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid (34.00 g, 60 mmol) was dissolved in 200 ml of pyridine under a nitrogen atmosphere. Acetic acid anhydride (8.8 ml, 90 mmol) was added and the mixture was stirred at room temperature for 21/2 hours. The reaction mixture was allowed to cool to room temperature and the product was filtered off, and washed with petroleum ether. This gave 25.63 g (81%) of the title compound as yellow crystals. M.p. 229-231° C. MS(SP): m/z 527 (M+). 1H-NMR (CDCl3, and DMSO-d6, 300 MHz) δ: 1.47 (t, 3H); 3.20 (q, 2H); 5.18 (s, 2H); 5.59 (s, 2H); 7.19 (d, 2H); 7.30-7.55 (m, 9H); 7.62 (d, 2H); 7.79 (d, 2H); 7.98 (d, 1H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe product was filtered off
  3. washwashed with petroleum ether

Sources & evidence

ORD record
ord-53ae119941344ee6b56f8b5ba0619d47
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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