C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].[CH3:12][O:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:35]1[CH2:44][CH2:43][CH2:42][C:41]2[C:40]([C:45]#[N:46])=[CH:39][CH:38]=[CH:37][C:36]1=2.BrC1C=CC=C2C=1CCCC2=O>C1COCC1.O>[CH3:12][O:13][CH:14]=[C:35]1[CH2:44][CH2:43][CH2:42][C:41]2[C:40]([C:45]#[N:46])=[CH:39][CH:38]=[CH:37][C:36]1=2Sodium bis(trimethylsilyl)amide (2 mL, 4 mmol, 2M in THF) was added to a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (1.47 g, 4.3 mmol) in dry THF (20 mL) at 0° C. for 35 min and a solution of 5-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile [prepared from 5-bromo-tetralone following the procedure described in PCT publication WO2004/071389A2, Intermediate 41](490 mg, 2.86 mmol) in THF (10 mL) added over 10 min. The mixture was stirred at 0° C. for 2 h and at room temperature for 1 h. Water was added and the mixture was partitioned between EtOAc and brine. The organic layer was dried and concentrated. The crude product was purified via preparative-TLC (PE:EtOAc=10:1) to afford the title compound.
Loading…
