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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Acetyl-5-benzyloxy-2-(4benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

HRID 1422096
Notes
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Reaction equation

HRID 1422096 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:11]([CH:12]=[C:13]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:22][CH:21]=3)[C:14]=2[CH2:18][CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][C:35](=[O:38])[C:36]#[CH:37].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[C:35]([C:36]1[CH:37]=[C:12]2[N:11]3[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:10]=13)[C:14]([CH2:18][CH3:19])=[C:13]2[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:25]=1)(=[O:38])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15018Butyn-2-oneHCID 187070166-Benzyloxy-2-(4-benzyloxyphenyl)-1-ethylindolizine

Product 1

HCID 187070344-Acetyl-5-benzyloxy-2-(4benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizineYield 38%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

6-Benzyloxy-2-(4-benzyloxyphenyl)-1-ehtylindolizine, prepared in example 23, step 5, (2.17 g, 5.0 mmol) was dissolved in 100 ml of dry toluene under a nitrogen atmosphere, and the mixture was stirred in an ice bath, while 3-butyn-2-one (0.34 ml, 5.75 mmol) was added dropwise. The cooling source was removed and stirring was continued for twenty hours. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (0.57 g, 0.25 mmol) was added in portions and stirring was continued for 11/2 hour. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using 20% of ethyl acetate in petroleum ether as the eluent. Fractions containing the product were colleted and the solvent was evaporated. The crude product was and crystallized from diethyl ether to afford 0.955 g (38%) of 4-acetyl-5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethylpyrrolo[2,1,5-cd]indolizine as crystals. MS(SP): m/z 499 (M+). 1H-NMR (CDCl3, 400 MHz) δ: 1.44 (t, 3H); 2.79 (s, 3H); 3.15 (q, 2H); 5.15 (s, 2H); 5.44 (s, 2H); 7.15 (d, 2H); 7.32-7.46 (m, 7H); 7.50 (d, 2H); 7.60 (d, 2H); 7.67-7.74 (m, 3H); 7.94 (s, 1H).

Workup

  1. additionwas added dropwise
  2. customThe cooling source was removed
  3. waitwas continued for twenty hours
  4. stirringstirring
  5. custom2 hour
  6. customThe solvent was evaporated
  7. customthe crude product was purified by column chromatography over silica gel 60
  8. additionFractions containing the product
  9. customthe solvent was evaporated
  10. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-4b52fed64f604825b7c76e6812253b91
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06080754

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes