Butyn-2-one → 4-Acetyl-2-(4-benzyloxyphenyl)-7-(tert-butyldimethylsilanyloxymethyl)-1-ethylpyrrolo[2,1,5-cd]indolizine

HRID 1422111Notes

Reaction equation

HRID 1422111 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:33][CH3:34])=[C:17]3[N:22]([CH:23]=2)[CH:21]=[CH:20][CH:19]=[C:18]3[CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][C:36](=[O:39])[C:37]#[CH:38]>>[C:36]([C:37]1[CH:38]=[C:23]2[N:22]3[C:17](=[C:18]([CH2:24][O:25][Si:26]([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:27])[CH3:28])[CH:19]=[CH:20][C:21]=13)[C:16]([CH2:33][CH3:34])=[C:15]2[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)(=[O:39])[CH3:35]

Participants

3

Reactant 2

HCID 15018Butyn-2-oneHCID 187069342-(4-Benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-1-ethylindolizine

Product 1

HCID 187070364-Acetyl-2-(4-benzyloxyphenyl)-7-(tert-butyldimethylsilanyloxymethyl)-1-ethylpyrrolo[2,1,5-cd]indolizineYield 70%

Procedure

2-(4-Benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-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-benzyloxyphenyl)-7-(tert-butyldimethylsilanyloxymethyl)-1-ethylpyrrolo[2,1,5-cd]indolizine as a brown oil in 70% yield. 1H--NMR (DMSO-d6, 200 MHz) δ: 0.13 (s, 6 H); 0.89 (s, 9 H); 1.37 (t, 3 H); 2.64 (s, 3 H); 3.18 (q, 2 H); 5.20 (s, 2 H); 5.32 (s, 2 H); 7.12-7.54 (m, 7 H); 7.73 (d, 2 H); 7.94 (d, 1 H); 8.18 (s, 1 H); 8.34 (d, 1 H).

Sources & evidence

ORD record
ord-f5d29a91833d47448dc9adbc611b83c7
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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