Hydrochloric Acid → (Z)-9-(Triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine

Participants

Reaction Conditions

Reaction Steps

Hydrogen chloride (5.64 mL, 11.28 mmol) (10 mL, 2M diethyl ether solution) was added to the CH2Cl2 (25 mL) solution of 2-(1-(triisopropylsilyloxy)pent-4-enyl)-3-vinylpyridine (3.9 g, 11.28 mmol). The solvent was removed via vacuum and the corresponding HCl salt was azeotroped by benzene twice. The reaction was charged with CH2Cl2 (500 mL) and purged with N2 for 10 min before addition of Grubb II (0.192 g, 0.226 mmol). The reaction was heat to 40° C. for 3 hours, LCMS showed no starting material left. The reaction was washed with saturated NaHCO3 solution once. The CH2Cl2 was separated, dried (Na2SO4), filtered and concentrated. Flash column by ether in hexane from 0 to 25% gave the desired product as yellow oil (2.54 g, 71% yield). MS (ESI)[M+H+]=318.35.

Provenance & Evidence