Water → 2-{2-[Hydroxy-(3,4,5trimethoxyphenyl)methyl]-4-methoxyphenyl}-4,4-dimethyl-2-oxazoline

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Reaction Conditions

Reaction Steps

A solution of 2-(4-methoxyphenyl)-4,4-dimethyl-2-oxazoline (11.0 g) in tetrahydrofuran (50 ml) is cooled to −50° C., and thereto is added dropwise a 1.6 M solution of n-butyl lithium in hexane (36.8 ml) over a period of 20 minutes. The mixture is stirred at 40° C. for 30 minutes, and thereto is added dropwise a solution of 3,4,5-trimethoxybenzaldehyde (10.5 g) in tetrahydrofuran (30 ml) at the same temperature over a period of 10 minutes. After reaction at −30T for one hour, to the mixture are added water and ethyl acetate. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give 2-{2-[hydroxy-(3,4,5trimethoxyphenyl)methyl]-4-methoxyphenyl}-4,4-dimethyl-2-oxazoline (16.2 g) as listed in Table 53.

Provenance & Evidence