Carbon Tetrachloride → HCID 86614067, compound

Participants

Reaction Conditions

Reaction Steps

To dry lithium chloride (1.0 g) in tetrahydrofuran (45 ml) was added n-butyllithium (4.75 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 10 min and then cooled to −78° C. before adding diethylchloromethyl phosphonate (1.85 ml) in tetrahydrofuran (13 ml). After stirring for 10 min, carbon tetrachloride (1.15 ml) in tetrahydrofuran (13 ml) was added. After stirring for a further 10 min, a solution of 3aS,4R,6aS,7R,10S,10aS)-7-acetyl-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 148, 2 g) in tetrahydrofuran (13 ml) was added and the solution was stirred for 2 h at −78° C. After this time the mixture was quenched into water (50 ml) and extracted with diethyl ether (3×50 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give an orange oil. The oil was purified by flash, chromatography using a Biotage® cartridge (90 g) to give the title compound as a transparent oil (1.05 g, 45%).

Provenance & Evidence