Formaldehyde → HCID 19902683, compound

Participants

Reaction Steps

To a solution of 1.0 g of 9-triisopropylsilylfluorene in 10 mL of dry ether and 30 mL of dry hexane was added dropwise 2.5 mL of 1.5M n-butyllithium. The mixture was refluxed for 15 hours and cooled in an ice bath. Gaseous formaldehyde, generated by heating dried paraformaldehyde at 170° C., was passed through a 8-mm tube into the reaction mixture with the aid of a slow stream of nitrogen until the deep red color had faded to pale yellow (ca. 5 min). The mixture was quenched immediately with 40 mL of half sat'd NH4Cl and washed with brine (10 mL) and water (20 mL). The pooled aqueous layer was extracted with ether (2×20 mL). The combined organic extracts were dried over MgSO4 and the solvent was evaporated in vacuo to give an oil which was chromatographed on silica gel (230-400 mesh, 2×40-cm packed column) with an eluant consisting of Skelly B--ether (3:1), to afford 0.63 g (57.7%) of the alcohol as a white solid. Recrystallization from Skelly F gave 0.38 g (34.8%) of the pure 9-triisopropylsilyl-9-fluorenemethanol as colorless crystals m.p. 106°-107.5° C.; IR (KBr): 3505, 3405 cm-1 (OH); 1H NMR (CDCl3): δ 0.83 (d, 18H, Si-C-Me2), 1.20-1.42 (hept, 3H, C--S--CH), 4.71 (s, 2H, CH2), 7.20-7.95 (m, 8H, aryl).

Provenance & Evidence