Boron trifluoride etherate → 3-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-ol

HRID 460467Notes

Reaction equation

HRID 460467 reaction equation
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[OH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]2[C@H:24]3[C@H:33]([CH2:34][CH2:35][C@:19]12[CH3:20])[C:32]1[CH:31]=[CH:30][C:29]([O:36][CH3:37])=[CH:28][C:27]=1[C:26](=O)[C@H:25]3[CH2:39][CH:40]=[CH2:41].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:37][O:36][C:29]1[CH:30]=[CH:31][C:32]2[C@@H:33]3[C@H:24]([C@H:21]4[C@@:19]([CH2:35][CH2:34]3)([CH3:20])[C@@H:18]([OH:17])[CH2:23][CH2:22]4)[C@H:25]([CH2:39][CH:40]=[CH2:41])[CH2:26][C:27]=2[CH:28]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 6941500617beta-Hydroxy-3-methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-6-one

Product 1

HCID 694148073-Methoxy-7alpha-(2-propenyl)estra-1,3,5(10)-trien-17beta-olYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (5 ml) and boron trifluoride diethyl etherate (5 ml) were added to a solution of 17β-hydroxy-3-methoxy-7α-(2-propenyl)estra-1,3,5(10)-trien-6-one (1.0 g, 2.9 mmol) in dichloromethane (20 mL) at 0° C. The resulting mixture was warmed to room temperature and stirred for 18 hours. After the reaction was completed, 10% aqueous potassium carbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then filtered. After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 3-methoxy-7α-(2-propenyl)estra-1,3,5(10)-trien-17β-ol (935 mg, Yield 98%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationAfter concentration under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-eccf79cfe1e0492480a68d53b10a2594
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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