Diisopropylamine → 4-(((4-bromophenyl)sulfonyl)methyl)tetrahydro-2H-pyran-4-ol

Participants

Reaction Steps

A −10° C. solution of diisopropylamine (0.35 mL) in THF (5 mL) was treated with n-BuLi (1 mL, 2.5M solution in hexanes), stiired for 15 min then added via canula to a −78 C solution of 4-bromophenyl methyl sulfone (534 mg) in THF (5 mL). Stirred for 1 h, then treated with tetrahydropyran-4H-pyran-4-one (0.21 mL) and stirred for an additional 1 h. The reaction was quenched with aq. NH4Cl, diluted with water and extracted wth EtOAc (3×). The combined organics were washed with brine, dried (Na2SO4), filtered, concentrated and purified via silica gel chromatography eluting with 10% ethyl acetate/dichloromethane to give 640 mg of the title compound.

Provenance & Evidence