Dimethyl Sulfoxide → HCID 58833525, compound

Participants

Reaction Steps

4.52 g (113 mmol) of NaH as a 60% strength dispersion in mineral oil were placed in a dry apparatus, 40 ml of dry DMSO were added, 36.8 g (75.4 mmol) of 2,7-dibromo-10-methoxy-10-methyl-9-p-tolyl-9,10-dihydrophenanthren-9-ol in 100 ml of dry DMSO were subsequently added dropwise and the mixture was stirred at RT for 30 minutes. 7 ml (113 mmol) of Mel were then added dropwise over a period of 1 hour while cooling in ice and the mixture was stirred at RT for 1 hour. To work up the mixture, it was cooled to 5° C., 150 ml of 15% NH4OH were added dropwise, the precipitate was filtered off with suction, washed twice with water and twice with MeOH. To purify it further, it was recrystallized four times from EtOH/toluene. This left 16.7 g (44%) of colorless crystals having a purity determined by RP-HPLC of 99.90%.

Provenance & Evidence