Sodium hydride → 1-(3-Propoxy-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanone

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Reaction Steps

To a solution of 1-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Intermediate 4, 6.4 g, 26 mmol) in DMF (100 mL) at 0° C. was added NaH (1.2 g, 60%, 31 mmol). After stirring for 30 min, PrI (3.0 mL, 31 mmol) was added. The reaction was stirred at 0° C. for 4 h, was quenched with aqueous NH4Cl and extracted with Et2O (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo.

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