Hydrogen Peroxide → HCID 87735465, compound

Participants

Reaction Steps

A solution of the compound of example 76 (1.03 g, 1.66 mmol) in a mixture of THF/water (4:1, 20 mL) was cooled in an ice bath and treated drop wise with a hydrogen peroxide solution (30%, 0.7 mL). After 5 minutes, a solution of lithium hydroxide monohydrate (1M, 6.6 mL, 6.6 mmol) was added over a period of 10 minutes. The reaction was completed following 2 h of stirring in the ice bath. At this stage, an aqueous solution of sodium sulfite (850 mg, 6.64 mmol, 5 mL) was added. The ice bath was removed and the reaction mixture was stirred for another 30 minutes. Most of the solvent was removed by evaporation and the residue was extracted with ether. The alkaline phase was acidified with HCl (6M) to pH˜1 and extracted three times with ethyl acetate. The recombined organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The desired product was obtained as a colorless oil. 1H-NMR (CDCl3, 400 MH: 1.40(s, 9H); 1.85(m, 4H); 2.27, 2.58(2dd, J1=16.5 Hz. J2=5.6 Hz, 4H); 2.84(m, 1H); 4.98(m, 4H); 7.31(m, 10H). 31P-NMR (CDCl3, 400 MHz): 33.14.

Provenance & Evidence