Triphenylphosphine → HCID 59578574, compound

Participants

Reaction Steps

Under nitrogen atmosphere, a solution of 6-chloro-2-(3-hydroxypropyl)-3-methylphenol (7c) (6.74 g, 33.6 mmol) in anhydrous tetrahydrofuran (500 mL) was cooled to 0° C. Triphenylphosphine (11.45 g, 43.7 mmol) was added, followed by diisopropyl azodicarboxylate (8.60 mL, 43.7 mmol). The reaction mixture was stirred for 16 hours at room temperature. After concentration in vacuo, the residue was dissolved in diethyl ether and the precipitate was filtered off. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 90/10), to provide 8-chloro-5-methyl-3,4-dihydro-2H-1-benzopyran (7d) (5.74 g, 31.4 mmol, 94%), as a light yellow oil.

Provenance & Evidence