Dimethyl acetylenedicarboxylate → HCID 18706949, compound

HRID 1422122Notes

Reaction equation

HRID 1422122 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:26][CH3:27])=[C:17]3[N:22]([CH:23]=2)[CH:21]=[C:20]([O:24][CH3:25])[CH:19]=[CH:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([C:34]([O:36][CH3:37])=[O:35])#[C:29][C:30]([O:32][CH3:33])=[O:31]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3=[C:28]([C:34]([O:36][CH3:37])=[O:35])[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:21]4[C:20]([O:24][CH3:25])=[CH:19][CH:18]=[C:17]([N:22]34)[C:16]=2[CH2:26][CH3:27])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 18707023HCID 18707023, compound

Product 1

HCID 18706949HCID 18706949, compoundYield 80%

Procedure

The general synthetic pathway outlined in example 23, step 1-5, have been applied to proper starting materials in the preparation of 2-(4-benzyloxyphenyl)-1-ethyl-6-methoxyindolizine, which was reacted with dimethyl acetylene dicarboxylate by the general synthetic principle outlined in example 23, step 6, to afford dimethyl 3-(4-benzyloxyphenyl)-4-ethyl-7-methoxypyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate as a red oil in 80% yield. 1H-NMR (CDCl3, 200 MHz) δ: 1.36 (t, 3H); 3.02 (q, 2H); 3.60 (s, 3H); 3.98 (s, 3H); 4.14 (s, 3H); 5.15 (s, 2H); 7.04-7.52 (m, 10H); 7.81 (d, 1H).

Sources & evidence

ORD record
ord-9a95528616dc4c4a98bf51e738930d1a
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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