Dichloromethane → HCID 68933064, compound

Participants

Reaction Steps

The compound of Example 16K (589 mg, 1.3 mmol) was dissolved in 20 mL of toluene and 10 mL of dichloromethane and cooled in a dry ice/acetone bath. Diisobutylaluminum hydride (1 M in hexanes, 5.8 mL, 5.8 mmol) was added dropwise. After 1 hour, the reaction was quenched by the addition of 20 mL of 20% aqueous sodium potassium tartrate. To this mixture was added 25 mL of water followed by 6 mL of 2 N HCl. The resulting mixture was extracted three times with dichloromethane. The combined extracts were washed with 10% aqueous NaCl, dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (70 mL of SiO2, elution with dichloromethane) afforded the titled compound (294 mg, 55%), contaminated with ˜20% of an olefin isomer.

Provenance & Evidence