Diethyl Ether → HCID 13436793, compound

Participants

Reaction Steps

Optimization of reaction conditions resulted in the following recommended procedure, illustrated for 1-methoxydec-2-ene as substrate. To a -78° solution of the substrate (0.1654 g, 0.92 mmole) in 20 ml CH2Cl2, under N2, was added TBHP (1.2 eq.), followed by TiCl4 (1.2 eq.). The reaction was worked up after 5 hr by pouring the cooled solution into Et2O/sat. Na2SO4 and allowing to stir for 1 hr. Separation of layers and purification of the crude product by chromatography resulted in a 92% yield of 1-methoxy-2-hydroxy-3-chlorodecane, with the chlorohydrin in the threo configuration.

Provenance & Evidence