4-tert-Butylphenylacetylene → Ethyl 6-(3-tert-butylphenylethynyl)nicotinate

HRID 36359Notes

Reaction equation

HRID 36359 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16](C(C)(C)C)=[CH:15][CH:14]=2)=[N:7][CH:6]=1)[CH3:2].[C:24](C1C=CC(C#C)=CC=1)([CH3:27])([CH3:26])[CH3:25]>>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=2)=[N:7][CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 27573024-tert-Butylphenylacetylene2×HCID 9861388Ethyl-6-(4-tert-butylphenylethynyl)nicotinate

Product 1

HCID 14989669Ethyl 6-(3-tert-butylphenylethynyl)nicotinate

Procedure

Using the same general procedure as described for Compound 3, but using instead 3-tert-butylphenylethyne (Compound 19), the title compound was synthesized as a white solid. PMR (CDCl3): & 1.34 (9H, s), 1.42 (3H, t, J~7.2 Hz), 4.43 (2H, q, J~7.2 Hz), 7.28-7.36 (1H, m), 7.40-7.46 (2H, m), 7.60 (1H, d, J~8.1 Hz), 7.67 (1H, s), 8.29 (1H, dd, J~8.1 Hz, 2.1 Hz), 9.21 (1H, d, J~2.1 Hz).

Sources & evidence

ORD record
ord-330f76b3e2a14f59aea7f4e22d1d1ae9
Source dataset
uspto-grants-1995_05
Patent number
US05414007

Reaction notes

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