Ethanol → ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate

HRID 1791469Notes

Reaction equation

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

Participants

Reactant 3

HCID 702Ethanol

HCID 65578Oxalyl chloride

HCID 220329371-Benzyl-5-phenyl-1H-indole

Product 1

HCID 22032978ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetateYield 66%

Procedure

Ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-phenyl-1H-indole (0.846 g, 2.99 mmol), oxalyl chloride (0.78 mL, 9.0 mmol), and ethanol (2 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage apparatus) using 5-7.5% ethyl acetate in hexane as an eluant yielded the title compound as a light yellow solid (0.754 g, 66%), mp: 116-117° C. Mass spectrum (+ES, [M+H]+) m/z 384; 1HNMR (500 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.4 (d, 1H, J=0.92 Hz), 7.6-7.7 (m, 3H), 7.55-7.6 (m, 1H), 7.45 (t, 2H, J=7.7 Hz), 7.3-7.4 (m, 6H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.1 Hz).

Workup

customPurification by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record: ord-137b44c12907427ba89083a530a22b08
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074817B2

Reaction notes

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