Toluene → HCID 11144022, compound

HRID 1422066Notes

Reaction equation

HRID 1422066 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

4

Reactant 3

HCID 1140TolueneHCID 6994510HCID 6994510, compoundHCID 11142002HCID 11142002, compound

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%.

Workup

  1. addition2,3-dichloro-5,6-dicyano-1,4-benzoequinone (1.84 g, 8.1 mmol) was added
  2. stirringstirring
  3. filtrationThe mixture was filtered through celite
  4. customthe solvent removed
  5. customThe crude product was purified by column chromatography over silica gel 60

Sources & evidence

ORD record
ord-8767111554474e198fbde6e8eb16dead
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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