Water → O-Benzyl-3,6,9-trioxacyclodecan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a refluxing suspension of sodium hydride (60% in mineral oil, pre-washed with hexane, 84 mg, 2.1 mmol) in dry THF (5 mL), a solution of 17 (182 mg, 1.0 mmol) and di(ethyleneglycol)dimethanesulfonate (260 mg, 1.0 mmol) in dry THF (5 mL) was added dropwise. The resulting mixture was heated under reflux for 20 h, afterward was cooled to 23° C. and H2O (2 mL) was added. The solvent was removed and the aqueous phase was extracted with CHCl3. The organic extracts were washed several times with water, dried (Na2SO4) and evaporated. The residue was purified by flash-chromatography (2:3 CH2Cl2/EtOAc) to afford 49 mg (19%) of 18 as a colourless oil: 1H NMR (CDCl3) δ 7.36-7.26 (m, 5H), 4.66 (s, 2H), 3.75-3.57 (m, 13H); MS (ESI) m/z 275 [M+Na]+.

Provenance & Evidence