alpha-Naphthaleneacetic acid, ethyl ester → Diethyl 2-dimethylamino-5-(1-naphthyl)-2,4-hexadienedioate

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Reaction Steps

The procedure is as in Example 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (10 g), a 2M ethanolic solution of sodium ethylate (26 cc) and ethyl 2-(1-naphthyl)acetate (7.5 g) in ethanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume), diethyl 2-dimethylamino-5-(1-naphthyl)-2,4-hexadienedioate (2.2 g) is obtained in the form of a yellow oil, and is used in the crude state in the subsequent syntheses.

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