Toluene → HCID 66938091, compound

Participants

Reaction Steps

(1S,2E)-4-[(4-methoxybenzyl)oxy]-2-methyl-1-[(1S)-1-methylprop-2-en-1-yl]but-2-en-1-yl 3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(2S,4R,5S)-4-methyl-2-phenyl-5-vinyl-1,3-dioxolan-4-yl]pentanoate (1.10 g, 1.63 mmol) and 2,6-di-tert-butyl-4-methylphenol (35.9 mg, 0.16 mmol) were dissolved in anhydrous toluene under Ar atmosphere. The reaction solution was heated to reflux for one hour. An anhydrous toluene (330 ml) solution of the second generation Hoveyda-Grubbs catalyst; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium (102 mg, 0.16 mmol) was added to the reaction solution. After the reaction solution was heated to reflux for five hours, it was cooled to room temperature. The reaction solution was filtered with silica gel (Fuji Silysia, commercial name Chromatorex, NH, 200-350 mesh) and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=8:1) to obtain the title compound (486.1 mg) as a white solid. This was obtained as a colorless needle by recrystallization (hexane:ethyl acetate).

Provenance & Evidence