Sodium hydride → HCID 23523001, compound

Participants

Reaction Conditions

Reaction Steps

385 mg (1.74 mmol) of trimethylsulphoxonium iodide are added to a suspension of sodium hydride (28 mg, 1.16 mmol) in 1 mL of DMSO. The mixture is stirred for 40 minutes, followed by successive addition of 1 mL of THF and 186 mg of anhydrous lithium iodide. The mixture is stirred for a further 30 minutes, cooled to 0° C., and 39 mg (0.11 mmol) of (2S,3S,4R)-2-(cyclohex-1-enyl)-3-methoxy-4-p-methoxybenzyloxy-cyclohexanone dissolved in 0.5 mL of THF are added. The bath is removed and the reaction is allowed to continue for 40 minutes at room temperature. After adding pH 7 buffer, extracton and evaporation of the solvents, the product is purified by chromatography on a preparative silica plate (eluent: 1:1 ether/pentane) to give 19 mg (45%) of (3R,4S,5S,6R)-4-(cyclohex-1-enyl)-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2,5]octane in the form of a colourless oil.

Provenance & Evidence