Boron trifluoride etherate → HCID 15859118, compound

HRID 1383024Notes

Reaction equation

HRID 1383024 reaction equation
O1[C:3]23[C@:16]([CH3:21])([CH:17]=[CH:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:22])[CH2:9][CH2:8]2)[CH2:5][C:4]3=[CH2:23].B(F)(F)[F:25].CCOCC>C(OCC)C>[F:25][C:2]1[C:19](=[O:20])[CH:18]=[CH:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 15859119HCID 15859119, compound

Product 1

HCID 15859118HCID 15859118, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4,5-epoxy-6-methylenandrost-1-ene-3,17-dione (1.0 g) in diethyl ether (100 ether (100 ml) was treated with boron trifluoride etherate (1.4 ml) for 3 hours at room temperature. Then the solution was washed with 5% sodium carbonate solution, water, dried (Na2SO4) and evaporated in vacuo. The residue was dissolved in pyridine (20 ml) and 0.4 ml of thionyl chloride were added at 0° C. After 5 minutes water was added and the product isolated with ether. The ether extracts were washed with 2N hydrochloric acid, water, dried (Na2SO4) and evaporated. The resulting raw product was chromatographed on silica gel using hexane/ethyl acetate as eluant to yield 0.6 g of pure 4-fluoro-6-methylenandrosta-1,4-diene-3,17-dione. Found: C 76.30; H 7.35; F 5.91; C20H23FO2 requires: C 76.40; H 7.37; F 6.04.

Workup

  1. washThen the solution was washed with 5% sodium carbonate solution, water
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in pyridine (20 ml)
  5. addition0.4 ml of thionyl chloride were added at 0° C
  6. additionAfter 5 minutes water was added
  7. customthe product isolated with ether
  8. washThe ether extracts were washed with 2N hydrochloric acid, water
  9. dry with materialdried (Na2SO4)
  10. customevaporated
  11. customThe resulting raw product was chromatographed on silica gel

Sources & evidence

ORD record
ord-357d0ba7fbfb478793014c98ed7989fd
Source dataset
uspto-grants-1989_02
Patent number
US04808616

Reaction notes

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