Benzoyl chloride → HCID 23072363, compound

HRID 1182466Notes

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]C=C[CH:3]=1.C(Cl)(=[O:27])C1C=CC=CC=1>>[O:27]1[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]1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 10934282Ethyl 8-oxo-8-phenyloctanoate

Product 1

HCID 23072363HCID 23072363, compoundYield 24%

Procedure

Following a procedure analogous to that described above for 49a, but substituting 3-furanoyl chloride for benzoyl chloride, the title compound was obtained as a yellow oil in 24% yield: 1H NMR (300 MHz, CDCl3) δ 8.03 (m, 1H), 7.44 (m, 1H), 6.76 (m, 1H), 4.12 (q, J=6.9 Hz, 2H), 2.74 (t, J=7.5 Hz, 2H), 2.29 (t, J=7.5 Hz, 2H), 1.71 (m, 2H), 1.63 (m, 2H), 1.37 (m, 4H), 1.25 (t, J=6.9 Hz, 3H); 13C NMR (75.4 MHz, CDCl3) δ 14.18, 24.04, 24.69, 28.82(2), 34.18, 40.23, 60.13, 108.56, 127.69, 144.09, 146.98, 173.68, 195.10.

Sources & evidence

ORD record: ord-9c40e7559cb94fbeb6809234a129ed6e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288567B2

Reaction notes

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