3-Methylcyclopentanone → HCID 9812946, compound

HRID 1835813Notes

Reaction equation

HRID 1835813 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) δ 8.56 (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-e75fe18685d34001a38a2cd5bde0b6fc
Source dataset
uspto-grants-2004_08
Patent number
US06774138B2

Reaction notes

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