Methane, dichloromethoxy- → HCID 23333166, compound

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Reaction Steps

5 g of 6-Cyclohexyl-2,3-dihydro-benzofuran are dissolved in methylene chloride. 9.5 ml of TiCl4 are slowly added dropwise whilst cooling and stirring, followed by 2.9 g of dichloromethylmethylether in 10 ml of Ch2Cl2. The mixture is stirred for 5 hours at 22°, poured onto ice-water and extracted with ethyl acetate. The organic phase is washed with water, dried over Na2SO4 and reduced in volume. The residue is dissolved in tetrahydrofuran without further purification. An excess of NaBH4 is added and the mixture refluxed for 3 hours. Natural working of the mixture yields 6-cyclohexyl-2,3-dihydro-5-hydroxymethyl-benzofuran.

Provenance & Evidence