Water → HCID 23436675, compound

Participants

Reaction Steps

Hexane washed sodium spheres (2.40 g, 104 mmol) were slowly added to 100 mL absolute ethanol. The sodium had fully reacted before cyclopentadiene (6.0 mL, 72.6 mmol) and 3,3,5,5-tetramethylcyclohexanone (10.0 mL, 57.1 mmol) were added. After 30 hours, the reaction was poured into 200 mL water and 100 mL diethyl ether were added. The organic layer was isolated and the aqueous layer was extracted with diethyl ether (3×50 mL). The combined organic layers were extracted with water (3×50 mL), dried over MgSO4, filtered, and rotavapped to produce the product in quantitative yield as a yellow oil. MS (GC-MS) m/z 202.3 (M+). 1H NMR (CDCl3): δ 0.97 (s, 12H, CH3), 1.04.(s, 2H, CH2), 2.39 (s, 4H, CH2), 6.52, 6.52 (m, 4H, fulvene-H).

Provenance & Evidence