Butyn-2-one → HCID 53780209, compound

HRID 1422119Notes

Reaction equation

HRID 1422119 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([CH2:25][CH3:26])=[C:18]3[N:23]([CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:27][C:28](=[O:31])[C:29]#[CH:30]>>[C:28]([C:29]1[CH:30]=[C:24]2[N:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=13)[C:17]([CH2:25][CH3:26])=[C:16]2[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[CH:11][CH:12]=1)(=[O:31])[CH3:27]

Participants

3

Reactant 2

HCID 15018Butyn-2-oneHCID 18707011HCID 18707011, compound

Product 1

HCID 53780209HCID 53780209, compoundYield 45%

Procedure

2-(4-(tert-Butyldimethylsilanyloxymethyl)phenyl)-1-ethylindolizine was reacted with 3-butyn-2-one by the general synthetic principles outlined in example 73, step 1, to afford 4-acetyl-2-(4-(tert-butyldimethylsilanyloxymethyl)phenyl)-1-ethylpyrrolo[2,1,5-cd]indolizine in 45% yield. 1H-NMR (CDCl3, 200 MHz) δ: 0.17 (s, 6H); 0.99 (s, 9H); 1.47 (t, 3H); 2.72 (s, 3H); 3.22 (q, 2H); 4.86 (s, 2H); 7.51 (d, 2H); 7.74 (d, 2H); 7.80-7.96 (m, 3H); 8.48 (dd, 1H).

Sources & evidence

ORD record
ord-f1de63bc860e45d88d2ecfbd9bdd4eb7
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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