Methyl iodide → HCID 22855814, compound

Participants

Reaction Conditions

Reaction Steps

Pivaloate 22 (3.52 g, 6.50 mmol) was dissolved in 50 ml of tetrahydrofuran at 25° C. and 523 mg of NaH (60% dispersion in mineral oil) and 4.0ml of anhydrous methyl iodide (10 equiv) were added successively. The solution was stirred at 25° C. for 24 hr. The mixture was partitioned between 150 ml of diethyl ether and 50 ml of water. The aqueous phase was extracted with an additional 2×100 ml of ether. The organic phases were combined, washed with 100 ml of saturated sodium chloride solution and dried over magnesium sulfate. Concentration in vacuogave 3.82 g of 23 as a crude oil. The material was purified by column chromatography on 190 g of silica gel eluting with hexanes:ethyl acetate (8:1) to give 3.58 g (99%) of dimethoxy pivaloate 23. This material was homogeneous by 1H and 13C NMR.

Provenance & Evidence