Bis(2-chloroethyl) ether → 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

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Reaction Steps

To a solution of 4-methoxyphenylacetonitrile (5 g, 34 mmol) and NaH (2.8 g, 71 mmol) in DMSO (50 ml) was added 2-chloroethyl ether (5.3 g, 37 mmol) with cooling. The mixture was stirred at room temperature for 3 h, quenched with water, and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated in vacuo to give an oil which was purified by a column chromatography to give Compound 88 (5.3 g, 24 mmol, 71%) as a colorless oil.

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