Ethynylpyridine → 2-{[(1R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]ethynyl}pyridine

HRID 902076Notes

Reaction equation

HRID 902076 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[C@:9]12([CH3:19])[C:16]([CH3:18])([CH3:17])[CH:13]([CH2:14][CH2:15]1)[CH2:12][C:10]2=O>>[CH3:19][C@:9]12[C:16]([CH3:18])([CH3:17])[CH:13]([CH2:14][CH2:15]1)[CH:12]=[C:10]2[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 137268EthynylpyridineHCID 9543187Npc54264

Product 1

HCID 98134732-{[(1R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]ethynyl}pyridine

Procedure

Reactants: 2-ethynylpyridine (6.0 mmol, 618 mg), (1R)-(+)-camphor (6.0 mmol, 912 mg); yields 2-{[(1R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-e-n-2-yl]ethynyl }pyridine as a transparent yellow oil (125 mg, 9% overall yield). 1H NMR (CDCl3, 300 MHz) Δ8.57 (m, 1H), 7.64 (m, 1H), 7.43 (m, 1H), 7.17 (m, 1H), 6.49 (d, J=3 Hz, 1H), 2.41 (t, J=3 Hz, 1H), 1.92 (br m, 1H), 1.65 (m, 1H), 1.18 (m, 1H), 1.17 (s, 3H), 1.09 (br m, 1H), 0.84 (s, 3H), 0.82 (s, 3H). MS (EI ionization) 237 (M+).

Sources & evidence

ORD record
ord-0e9989d64d194b02a5b9518a74570e78
Source dataset
uspto-grants-2008_04
Patent number
US07365074B2

Reaction notes

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