Hydrogen Peroxide → HCID 66640067, compound

Participants

Reaction Steps

21 ml (0.22 Mol) borane dimethylsulfide complex are added dropwise during 15 min to an ice-cooled solution of 50.2 ml (495 mMol) cyclohexene in 400 ml of THF. The mixture is stirred for 2.5 h at rt and again cooled in an ice-bath. Then a solution of 23.29 g (82.5 mMol) trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester in 400 ml of THF is added dropwise. The mixture is warmed up to rt and stirred for 1 h. Then 585 ml sat. NaHCO3 solution and 138 ml H2O2 (30% in H2O) are added slowly (cool to keep temperature below 60° C.). The suspension is stirred for 16 h and then concentrated in vacuo. The residue is diluted with 1 l sat. NaHCO3 solution, 375 ml water and EtOAc, the organic layer is separated off and washed with 0.5 l sat. NaHCO3 solution and 250 ml water and discarded. The aq. phases are acidified by addition of 4 N HCl (pH=2) and extracted with 3 portions of EtOAc. The organic layers are dried (MgSO4) and concentrated. Trituration from hexane affords the title compound: MS: [M+1]+=245; HPLC: tRet=12.3.

Provenance & Evidence