Ethynylpyridine → 2-[(3,5-Dimethyl-1-cyclohexen-1-yl)ethynyl]pyridine

HRID 1835818Notes

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[CH2:15][CH:14]([CH3:16])[CH2:13][C:12](=O)[CH2:11]1>>[CH3:9][CH:10]1[CH2:15][CH:14]([CH3:16])[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

Reactant 2

HCID 137268Ethynylpyridine

HCID 1375443,5-Dimethylcyclohexanone

Product 1

HCID 98343262-[(3,5-Dimethyl-1-cyclohexen-1-yl)ethynyl]pyridine

Procedure

Reactants: 2-ethynylpyridine (6.0 mmol, 618 mg), 3,5-dimethylcyclohexanone (6.0 mmol, 0.85 mL); yields 2-[(3,5-dimethyl-1-cyclohexen-1-yl)ethynyl]pyridine as a transparent yellow oil (500 mg, 39% overall yield) as a mixture of diastereomers. 1H NMR (CDCl3, 300 MHz) δ 8.57 (m, 1H), 7.62 (m, 1H), 7.40 (m, 1H), 7.19 (m, 1H), 6.15 (br s, 1H), 2.29 (m, 2H), 1.80 (br m, 2H), 1.00 (m, 6H), 0.88 (br m, 2H). MS (EI ionization) 211 (M+).

Sources & evidence

ORD record: ord-9a65929abe654dc6a62262c5fb3141df
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774138B2

Reaction notes

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