Cycloheptanone → HCID 68654371, compound

HRID 229274Notes

Reaction equation

HRID 229274 reaction equation
[C:1]1(=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=O)=[CH:13][CH:12]=1>>[C:1]1(=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10400CycloheptanoneHCID 108683214-(4-Methoxybenzoyl)benzonitrile

Product 1

HCID 68654371HCID 68654371, compoundYield 56.3%

Procedure

The general McMurry protocol, described for 14 was employed. The coupling was conducted between cycloheptanone (1.5 mL, 12.64 mmol), and 4-{[4-(methyloxy)phenyl]carbonyl}benzonitrile (1.0 g, 4.2 mmol) to afford 0.750 g (56%) of the title compound 207 as a white solid. IR (film): 2920, 2225, 1603, 1508, 1242, 825, cm1. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, J=8.1 Hz, 2H), 7.25 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 3.80 (s, 3H), 2.36 (br s, 2H), 2.29 (br s, 2H), 1.60 (s, 8H).

Sources & evidence

ORD record
ord-13f72fb059cb4964876dd4853020f6f4
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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