3-Methylcyclopentanone → HCID 9812946, compound

HRID 2374191Notes

Reaction equation

HRID 2374191 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[CH3:9][CH:10]1[CH2:14][CH2:13][C:12](=O)[CH2:11]1>>[CH3:9][CH:10]1[CH2:14][C:13]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:12][CH2:11]1.[CH3:9][CH:10]1[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

Participants

4

Reactant 2

HCID 156503-MethylcyclopentanoneHCID 137268Ethynylpyridine

Product 2

HCID 9812946HCID 9812946, compoundHCID 9942319HCID 9942319, compound

Procedure

Reactants: 2-ethynylpyridine (620 mg, 6.0 mmol), 3-methylcyclopentanone (0.64 mL, 6.0 mmol); yields 2-[(4-methyl-1-cyclopenten-1-yl)ethynyl]pyridine and 2-[(3-methyl-1-cyclopenten-1-yl)ethynyl]pyridine (1:1) as a transparent oil (200 mg, 18% overall yield), as mixture of regio- and stereoisomers. 1H NMR (CDCl3, 300 MHz) Δ8.56 (m, 1H), 7.64 (m, 1H), 7.44 (m, 1H), 7.20 (m, 1H), 6.19 (m, 0.5H), 6.18 (m, 0.5H), 2.90 (m, 0.5H), 2.70 (m, 2.5H), 2.21 (m, 2H), 1.48 (m, 0.5H), 1.08 (app d, J=7.5 Hz, 3H). Two peaks: 182 (M+), 167 (M+−Me).

Sources & evidence

ORD record
ord-98ec1b0f1bd94cdea3532138eeebaa28
Source dataset
uspto-grants-2008_12
Patent number
US07462619B2

Reaction notes

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