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

HRID 902077

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) 67 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-12b4b581055c4b2d9e6e9c640a19a65c
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365074B2

Linked notes

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