Cesium fluoride → 6-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(2-cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxom-4-one (−27.5 mmol, crude material from step 1 above), CsF (7.6 g, 50.0 mmol), and MeOH (75 mL) was stirred at room temperature overnight. HPLC at this time still showed starting material, so the reaction was heated at 40° C. for an additional 4 hours, at which time all starting material had been consumed. The reaction was concentrated and purified by flash chromatography through silica, eluted with 30% ethylacetate/hexanes, yielding 4.0 g of product (61% yield for two steps). 1H NMR (CDCl3): δ 1.63 (m, 4H), 1.72 (s, 3H), 1.74 (s, 3H), 2.16 (m, 1H), 2.49 (s, 1H), 2.53 (s, 1H), 2.58 (s, 1H), 5.43 (s, 1H), ESIMS (M+Na+): 287.1.

Provenance & Evidence