Cl[C:2]1[N:3]=[C:4]([CH2:15][OH:16])[CH:5]=[C:6]2[CH:10]=[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]=12.C1CCCCC=1>[Pd].CCO>[OH:16][CH2:15][C:4]1[CH:5]=[C:6]2[CH:10]=[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]2=[CH:2][N:3]=1C5 (1.05 g, 4.1 mmol) and 10% Pd/C catalyst (1.05 g) are placed in 20 mL absolute EtOH. Cyclohexene (4 mL, 40.1 mmol) is added, and the reaction is refluxed for 2.5 h, and then filtered through celite. The filter cake is washed with 1:1 EtOH/CH2Cl2, and the filtrate is concentrated to a pale yellow solid. The residue is partitioned between 40 mL saturated NaHCO3 and extracted with CH2Cl2 (4×20 mL). The combined organic layer is dried over MgSO4, filtered, and then concentrated in vacuo to a pale oil (1.04 g). The pale oil is chromatographed over 50 g silica gel (230-400 mesh) eluting with 50-70% EtOAc/hexane to afford 5-hydroxymethyl-2-trimethylsilyl-furo[2,3-c]pyridine (C14) as a white solid (90% yield). MS (EI) for C11H15NO2Si, m/z: 221(M)+.
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