(+)-3-Methylcyclohexanone → HCID 69221234, Verbindung

Reaktionsgleichung

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[CH3:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]1>>[CH3:9][C@H:10]1[CH2:11][C:12]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:13][CH2:14][CH2:15]1.[CH3:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C:12]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:11]1

Komponenten

Edukt 2

HCID 83384(+)-3-Methylcyclohexanone

HCID 137268Ethynylpyridine

Produkt 2

HCID 69221234HCID 69221234, Verbindung

HCID 69221747HCID 69221747, Verbindung

Versuchsvorschrift

Reactants: 2-ethynylpyridine (6.0 mmol, 618 mg), (3R)-(+)-3-methylcyclohexanone (6.0 mmol, 0.73 mL); yields 2-{[(5R)-5-methyl-1-cyclohexen-1-yl]ethynyl}pyridine and 2-{[(3R)-3-methyl-1-cyclohexen-1-yl]ethynyl}pyridine (1:1) as a transparent yellow oil (440 mg, 37% overall yield) as a mixture of regioisomers. 1H NMR (CDCl3, 300 MHz) Δ8.56 (m, 1H), 7.62 (m, 1H), 7.40 (m, 1H), 7.18 (m, 1H), 6.31 (m, 0.5H), 6.19 (m, 0.5H), 2.30 (m, 3H), 1.85 (m, 2.5H), 1.22 (m, 1H), 0.98 (m, 3.5H). MS (EI ionization) 197 (M+) two peaks resolved.