Methyl iodide → HCID 11557990, compound

Participants

Reaction Steps

A solution of tert-butyldimethylsilyl derivative of 5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-3,6-diol (30 mg), prepared as described in Example 22, in 1 mL of THF was added to NaH (8 mg) suspended in THF (1.5 mL). The resulting mixture was stirred at room temperature for 10 min and methyl iodide (34 mg) was added. The reaction was stirred at room temperature for 10 h and quenched onto 30 g of ice. It was extracted with hexane/EtOAc (2:1, 3×30 mL) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to afford the 6-tert-butyldimethylsilyl derivative of 3-methoxy-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol which was used directly for the next reaction.

Provenance & Evidence