2-Phenylethanol → ethyl 2,3-dimethyl-1-(2-phenylethyl)-1H-indole-5-carboxylate

HRID 1015436Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2.[C:17]1([CH2:23][CH2:24]O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(C=C1CCP(C)C1(C)C)#N>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A 211 mg portion of ethyl 2,3-dimethyl-1H-indole-5-carboxylate was dissolved in 10 ml of toluene, and 0.232 ml of 2-phenylethanol and 224 mg of cyanomethylene trimethylphospholan were added at room temperature, followed by stirring at 100° C. for 17 hours. After evaporation of the solvent under a reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:49 to 1:9) to obtain 107 mg of ethyl 2,3-dimethyl-1-(2-phenylethyl)-1H-indole-5-carboxylate as a colorless oily material.

Workup

customAfter evaporation of the solvent under a reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:49 to 1:9)

Sources & evidence

ORD record: ord-5b1399b305974b06951770ab3ccf60b2
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985764B2

Reaction notes

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