Ethanol → Ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate

HRID 2221237Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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 220329241-Benzyl-6-phenyl-1H-indole

Product 1

HCID 86588621Ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetateYield 77%

Procedure

Ethyl (1-benzyl-6-phenyl-1H-indol-3-yl)(oxo)acetate was prepared from, 1-benzyl-6-phenyl-1H-indole (1.90 g, 6.71 mmol), oxalyl chloride (1.8 mL, 20 mmol), and ethanol (4 mL). Purification by flash chromatography, using 5-12.5% ethyl acetate in hexane as an eluant, yielded the title compound as a light yellow solid (1.98 g, 77%), mp: 121-123° C. Mass spectrum (+ES, [M+H]+) m/z 384; 1HNMR (500 MHz, DMSO-d6): δ 8.7 (s, 1H), 8.25 (d, 1H, J=8.2 Hz), 7.9 (d, 1H, J=0.46 Hz), 7.7 (d, 2H, J=7.9 Hz), 7.65 (dd, 1H, J=8.2 H and 0.76 Hz), 7.45 (t, 2H, J=7.6 Hz), 7.35-7.4 (m, 5H), 7.25-7.35 (m, 1H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.1). Elemental Analysis for C25H17NO3: Calculated: C, 78.31; H, 5.52; N, 3.65. Found: C, 77.93; H, 5.40; N, 3.58.

Workup

customPurification by flash chromatography

Sources & evidence

ORD record: ord-2b6c22f4e31d4dc3a0b304b3852cf70f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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