Methyl Ethyl Ketone → HCID 9942206, compound

HRID 1835820Notes

Reaction equation

HRID 1835820 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[CH3:9][C:10](=O)[CH2:11][CH3:12]>>[CH3:9]/[C:10](=[CH:11]\[CH3:12])/[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH2:11]([C:10](=[CH2:9])[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:12].[CH3:9]/[C:10](=[CH:11]/[CH3:12])/[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 6569Methyl Ethyl KetoneHCID 137268Ethynylpyridine

Product 3

HCID 9942206HCID 9942206, compoundHCID 9964165HCID 9964165, compoundHCID 23500884HCID 23500884, compound

Procedure

Reactants: 2-ethynylpyridine (6.0 mmol, 618 mg), 2-butanone (6.0 mmol, 0.54 mL); yields 2-[(3E)-3-methyl-3-penten-1-ynyl]pyridine, 2-(3-ethyl-3-buten-1-ynyl)pyridine and 2-[(3Z)-3-methyl-3-penten-1-ynyl]pyridine as a transparent oil (135 mg, 14% overall yield) as a mixture of E, Z and exo-methylene isomers. 1H NMR (CDCl3, 300 MHz) δ 8.59 (m, 1H), 7.65 (m, 1H), 7.44 (m, 1H), 7.20 (m, 1H), 5.88 (m, 0.75H), 5.53 (s, 0.33H) 5.40 (s, 0.33H), 2.29 (q, J=7 Hz, 0.65H), 1.93 (m, 4.5H), 1.17 (t, J=7 Hz, 1H). MS (EI ionization) 157 (M+) two peaks resolved.

Sources & evidence

ORD record
ord-4a009e68d9564e99bccad23e54269a3a
Source dataset
uspto-grants-2004_08
Patent number
US06774138B2

Reaction notes

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