1,4-Dioxane → 5-Cyclopropyl-1-methyl-1H-indole

HRID 222478Notes

Reaction equation

HRID 222478 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.O1CCOC[CH2:14]1>C(OCC)C>[CH:11]1([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[CH:3]=[CH:4]3)[CH2:14][CH2:12]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 137379221H-Indole, 5-ethenyl-1-methyl-

Product 1

HCID 685240125-Cyclopropyl-1-methyl-1H-indoleYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-Methyl-5-vinyl-1H-indole (290 mg, 1.84 mmol) in dioxane (5 mL) was cooled at 0° C. and solution of CH2N2 in diethyl ether was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The solvents were evaporated and the residue was purified by column chromatography (ethyl acetate:hexane; 5:95) to give a product (305 mg, 96%). 1H NMR (CDCl3, 400 MHz) 0.68 (m, 2H), 0.88 (m, 2H), 2.00 (m, 1H), 3.71 (s, 1H), 6.37 (d, J=2.9 Hz, 1H), 6.97 (m, 2H), 7.18 (d, J=8.4 Hz, 1H), 7.34 (s, 1H); 13C NMR (CDCl3, 100 MHz) 8.5, 13.6, 17.5, 32.8, 100.3, 108.9, 117.5, 120.4, 128.6, 128.9, 134.4, 135.3.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by column chromatography (ethyl acetate:hexane; 5:95)

Sources & evidence

ORD record
ord-7b47e23da6fa4a19b70f48da5920300c
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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