Butyl iodide → 2-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-butylpentyl]-1,4-difluorobenzene

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Reaction Steps

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.287 ml, 0.450 mmol) was added to a tetrahydrofuran (4 ml) solution of the 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene (200 mg, 0.409 mmol) obtained in Example 15. The temperature of the resulting mixture was raised to room temperature. After cooling to −78° C., hexamethylphosphoric triamide (0.214 ml, 1.23 mmol) and iodobutane (51.1 μl, 0.450 mmol) were added dropwise to the reaction mixture. The resulting mixture was stirred at room temperature for 20 hours. Isopropanol (0.5 ml) was added to the reaction mixture, followed by concentration. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (5% ethyl acetate-hexane), whereby the title compound (163 mg, 73%) was obtained as a colorless oil.

Provenance & Evidence