Benzoyl chloride → Ethyl 7-(4-biphenyl)carbonylheptanoate

HRID 1182464Notes

Reaction equation

[C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:5]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:7][C:2]([C:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:8])=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 10934282Ethyl 8-oxo-8-phenyloctanoate

Product 1

HCID 11782725Ethyl 7-(4-biphenyl)carbonylheptanoateYield 41%

Procedure

Following a procedure analogous to that described above for 49a, but substituting 4-biphenylcarbonyl chloride for benzoyl chloride, the title compound was obtained as a white solid in 41% yield: 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=7.2 Hz, 2H), 7.39-7.69 (m, 7H), 4.12 (q, J=6.9 Hz, 2H), 2.99 (t, J=7.2 Hz, 2H), 2.30(t, J=7.5 Hz, 2H), 1.76 (m, 2H), 1.65 (m, 2H), 1.40 (m, 4H), 1.25 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record: ord-df14a7bb42244bbca08991f7b7794b34
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288567B2

Reaction notes

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