Dimethyl Sulfoxide → HCID 58833525, compound

HRID 2241072Notes

Reaction equation

HRID 2241072 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([Br:18])=[CH:12][CH:13]=3)[C:8]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)([OH:19])[C:7]([O:28][CH3:29])([CH3:27])[C:6]=2[CH:5]=1.[NH4+].[OH-].[CH3:32]S(C)=O>>[Br:18][C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:6](=[CH:5][C:4]([Br:3])=[CH:17][CH:16]=3)[C:7]([O:28][CH3:29])([CH3:27])[C:8]([O:19][CH3:32])([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[C:9]=2[CH:10]=1

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 67524802HCID 67524802, compound

Product 1

HCID 58833525HCID 58833525, compound

Procedure

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%.

Workup

  1. additionwere added
  2. addition7 ml (113 mmol) of Mel were then added dropwise over a period of 1 hour
  3. temperaturewhile cooling in ice
  4. stirringthe mixture was stirred at RT for 1 hour
  5. temperaturewas cooled to 5° C.
  6. filtrationthe precipitate was filtered off with suction
  7. washwashed twice with water and twice with MeOH
  8. customTo purify it further
  9. customit was recrystallized four times from EtOH/toluene

Sources & evidence

ORD record
ord-86e97c4acabf43abb28c9db8c88ecbee
Source dataset
uspto-grants-2010_05
Patent number
US07723455B2

Reaction notes

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