Sodium hydride → 5-(5-Bromothiophen-2-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

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Reaction Steps

To a solution of 5-bromothiophen-2-ylmethanol (6.76 g, 35 mmol) in tetrahydrofuran (100 ml) at 0° C. is added, carefully, sodium hydride, 60% dispersion in mineral oil, (1.2 g, 30 mmol over a period of 10 minutes. The reaction is allowed to warm to room temperature and stirred for a further hour. 5-Chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (5.02 mg, 25 mmol) is then added in one portion and the reaction mixture is allowed to stir at room temperature for 17 hours. The reaction is concentrated in vacuo and purified by flash chromatography on silica gel to give the desired compound as a white solid (4.45 g)

Provenance & Evidence