Allyl iodide → HCID 13286892, compound

HRID 1721433Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2.[CH2:16](I)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2)[CH:17]=[CH2:16]

Participants

Conditions

Temperature: 50 °C

Procedure

50 mg (0.24 mmol) of ethyl 4-hydroxyindole-2-carboxylate (U.S. Pat. No. 3,705,907), 48 mg (0.29 mmol) of allyl iodide, and 33 mg (0.24 mmol) of potassium carbonate were added to 0.5 ml of N,N-dimethylformamide, and the mixture was stirred for 1 hour and 45 minutes at 50° C. After the reaction, the solvent was evaporated. The residue was dissolved in chloroform, washed with saturated aqueous solution of sodium hydrogen carbonate and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 63 mg of a crude product, which was purified by separation thin layer chromatography (silica gel, chloroform: methanol=30:1) to obtain 42 mg (yield: 70.2%) of the target compound. This compound was recrystallized from a mixture of chloroform and n-hexane to obtain light brown needles of the title compound.

Workup

customAfter the reaction
customthe solvent was evaporated
dissolutionThe residue was dissolved in chloroform
washwashed with saturated aqueous solution of sodium hydrogen carbonate and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated
customto obtain 63 mg of a crude product, which
customwas purified by separation thin layer chromatography (silica gel, chloroform: methanol=30:1)

Sources & evidence

ORD record: ord-521eca1b0a7743a1aa654461af2a66ff
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05510366

Reaction notes

Loading…