Water → 5,9-Dimethyl-9-triethylsilanyloxy-decanal

Participants

Reaction Conditions

Reaction Steps

To a solution of aldehyde 15 (16.5 mg, 82.5 μmol) and 2,6-lutidine (24 μL, 206 ,μmol) in anhydrous CH2Cl2 (1.1 mL) was added dropwise Et3SiOTf (42 μL, 165 μmol) at −78° C. The mixture was stirred for 2 hours at −78° C. and for one additional hour at −50° C. Water and CH2Cl2 were added, the organic layer was washed with water, dried over MgSO4, and evaporated. The residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (99.7:0.3) as an eluent to give oily aldehyde 16 (22 mg, 85%). An analytical sample was obtained using HPLC (10 mm ×25 cm Zorbax-Sil column, 4 mL/min) with a hexane/EtOAc (98:2) solvent system. Analytically pure aldehyde 16 was collected at Rv=33 mL.

Provenance & Evidence