AGN 193109 Ethyl Ester → Ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoate
Reaction equation
CC1(C)CC=C(C2C=CC(C)=CC=2)C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC1=2.[CH3:33][C:34]1([CH3:71])[CH2:43][CH:42]=[C:41]([C:44]2C=C[C:47]([O:50][Si](CC(C)C)(C)C)=[CH:46][CH:45]=2)[C:40]2[CH:39]=[C:38]([C:58]#[C:59][C:60]3[CH:70]=[CH:69][C:63]([C:64]([O:66][CH2:67][CH3:68])=[O:65])=[CH:62][CH:61]=3)[CH:37]=[CH:36][C:35]1=2>>[CH3:71][C:34]1([CH3:33])[CH2:43][CH:42]=[C:41]([C:44]2[O:50][CH:47]=[CH:46][CH:45]=2)[C:40]2[CH:39]=[C:38]([C:58]#[C:59][C:60]3[CH:70]=[CH:69][C:63]([C:64]([O:66][CH2:67][CH3:68])=[O:65])=[CH:62][CH:61]=3)[CH:37]=[CH:36][C:35]1=2Participants
Procedure
Employing the same general procedure as for the preparation of ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl)ethynyl]benzoate (Compound 1), 250.0 mg (0.52 mmol) of ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(trifluoromethylsulfonyl)oxy-2-naphthalenyl)ethynyl]benzoate (Compound G) was converted into the title compound (colorless solid) using 142.4 mg (1.045 mmol) of zinc chloride, 24.1 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium(0) and 2-lithiofuran (prepared by the addition of 53.4 mg (0.52 ml, 0.78 mmol) of n-butyllithium (1.5M solution in hexane) to a cold solution (−78° C.) of 53.4 mg (0.784 mmol) of furan in 1.0 ml of THF). PMR (CDCl3): δ1.32 (6H, s), 1.41 (3H, t, J=7.1 Hz), 2.35 (2H, d, J=5.0 Hz), 4.39 (2H, q, J=7.1 Hz), 6.41 (1H, t, J=5.0 Hz), 6.50 (2H, s), 7.36 (1H, d, J=8.0 Hz), 7.45 (1H, dd, J=1.7, 8.0 Hz), 7.49 (1H, s), 7.57 (2H, d, J=8.2 Hz), 7.63 (1H, d, J=1.7 Hz), 8.02 (2H, d, J=8.2 Hz).
Sources & evidence
- ORD record
- ord-a413e28ba76e47c8b416b47dab4e98ca
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06469028B1
Reaction notes
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