Toluene → HCID 11144022, compound

Reaction equation

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

Participants

Reactant 3

HCID 1140Toluene

HCID 6994510HCID 6994510, compound

HCID 111420022-(4-Benzyloxyphenyl)-1-ethylindolizine

Product 1

HCID 11144022HCID 11144022, compoundYield 58%

Procedure

A solution of 2-(4-benzyloxyphenyl)-1-ethylindolizine (6.55 g, 20 mmol) and methylpropiolate (10.4 g, 124 mmol) in 250 ml of dry toluene was heated to 100° C. under nitrogen atmosphere and stirred for 21/2 hour. The mixture was cooled to room temperature and 2,3-dichloro-5,6-dicyano-1,4-benzoequinone (1.84 g, 8.1 mmol) was added and stirring was continued for 1 our. The mixture was filtered through celite and the solvent removed. The crude product was purified by column chromatography over silica gel 60, using 20% of diethyl ether in hexane as the eluent to afford 4.82 g (58%) of methyl 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate. M.p. 129-131° C. MS(SP): m/z 409 (M+). 1H-NMR (CDCl3, 200 MHz) δ: 1.47 (t, 3H); 3.22 (q, 2H); 4.01 (s, 3H); 5.16 (s, 2H); 7.15 (d, 2H); 7.32-7.52 (m, 5H); 7.72 (d, 2H); 7.75-7.90 (m, 2H); 8.03 (s, 1H); 8.33 (dd, 1H). Analysis: Calculated for C27H23N1O3 : C, 79.20; H, 5.66; N, 3.42%; Found: C, 79.10; H, 5.50; N, 3.20%.