Toluene → HCID 9821134, compound

HRID 1654414Notes

Reaction equation

HRID 1654414 reaction equation
C1CO[C:8]23OCC[O:12][C:3]2([C@:4]2([CH:26]=C(OS(C(F)(F)F)(=O)=O)[C@H:24]4[C@@H:15]([CH2:16][CH:17]=[C:18]5[C@@H:23]4[CH2:22][CH2:21][CH2:20][CH2:19]5)[C@@H:6]2[CH2:7]3)[CH3:5])O1.[Cl-].[Li+].[C:37](=O)([O-])[O-:38].[Na+].[Na+].CC1C=CC(B(O)[OH:51])=CC=1.[Cl-].[Na+].[C:55]1([CH3:61])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C(O)C>[CH3:37][O:38][C:58]1[CH:59]=[CH:60][C:55]([C@H:61]2[CH2:5][C@@:4]3([CH3:26])[C@@H:6]([CH2:7][CH2:8][C:3]3=[O:12])[C@H:15]3[C@H:24]2[C@@H:23]2[C:22]([CH2:17][CH2:16]3)=[CH:21][C:20](=[O:51])[CH2:19][CH2:18]2)=[CH:56][CH:57]=1

Participants

8

Reactant 6

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 433294Lithium ChlorideHCID 86748216HCID 86748216, compound

Product 1

HCID 9821134HCID 9821134, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

17,17-bis-(ethylenedioxy)-11-trifluoromethylsulfonyloxy-5,11-estradiene is dissolved in a mixture of 31 ml of toluene and 14 ml of ethanol and mixed in succession with 0.2 g of palladiumtetrakistriphenylphosphine, 0.29 g of lithium chloride, 4.4 ml of 2 molar sodium carbonate solution and 0.5 g (3.7 mmol) of 4-methylphenylboronic acid. The reaction mixture is then stirred for 1 hour at 95° C., cooled to room temperature and mixed with saturated sodium chloride solution. The organic phase is separated, washed in succession with 5% sodium hydroxide solution and water, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane. 1.28 g of the title compound is obtained as white foam.

Workup

  1. temperaturecooled to room temperature
  2. customThe organic phase is separated
  3. washwashed in succession with 5% sodium hydroxide solution and water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue is chromatographed on silica gel with a mixture of ethyl acetate/hexane

Sources & evidence

ORD record
ord-c68edd1133884a48ad0b88b1622d6f81
Source dataset
uspto-grants-1995_04
Patent number
US05405979

Reaction notes

Loading…