3-Methylcyclopentanone → HCID 9812946, compound

HRID 902073Notes

Reaction equation

HRID 902073 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-d4b6c351cc7840d0a1a13bb469090cc3
Source dataset
uspto-grants-2008_04
Patent number
US07365074B2

Reaction notes

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