Butyn-2-one → HCID 18706958, compound

HRID 1422105Notes

Reaction equation

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

Participants

Reactant 2

HCID 15018Butyn-2-one

HCID 18707005HCID 18707005, compound

Product 1

HCID 18706958HCID 18706958, compoundYield 14%

Procedure

1-Ethyl-8-benzyloxy-2-(4-benzyloxyphenyl)indolizine was reacted with 3-butyn-2-one by the general synthetic principles outlined in example 73, step 1, to afford the title compound as yellow crystals in 14% yield. M.p. 147-149° C. MS(SP): m/z 499 (M+). 1H--NMR (DMSO-d6, 200 MHz) δ: 1.37 (t, 3 H); 2.65 (s, 3 H); 3.16 (q, 2 H); 5.22 (s, 2 H); 5.53 (s, 2 H); 7.23 (d, 2 H); 7.33-7.83 (m, 13 H); 8.13 (s, 1 H); 8.28 (d, 1 H).

Sources & evidence

ORD record: ord-3adb35d1c717428cad4e07368d2804b7
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080754

Reaction notes

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