Boron trifluoride etherate → HCID 54732141, compound

HRID 2293679Notes

Reaction equation

HRID 2293679 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[CH:13]1[CH:14]=[CH:15][C:16]([C@H:19]2O[C@@H:20]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][CH:18]=1.B(F)(F)F.CCOCC>O1CCOCC1>[C:16]1([C:19]([C:3]2[C:4](=[O:12])[O:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 185583(R,R)-Stilbene oxideHCID 546829304-Hydroxycoumarin

Product 1

HCID 54732141HCID 54732141, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flame-dried flask containing a mixture of 650 mg of 4-hydroxycoumarin and 1.0 g of commercially available trans-stilbene oxide in 20 mL of dioxane under an argon atmosphere is added 2.5 mL of boron trifluoride etherate. The resulting yellow solution is left to stir at room temperature overnight. The volatiles are removed and the residue is partioned between diethyl ether and 1N sodium hydroxide. The basic aqueous phase is washed with diethyl ether and acidified to pH=1 with 6N hydrochloric acid. The resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform co-solvents). The combined dichloromethane extracts are washed once with dilute sodium bicarbonate to remove most of the unreacted 4-hydroxycoumarin, then brine, dried (magnesium sulfate), and finally concentrated under reduced pressure. The residue is flash column chromatographed with 50% to 66% ethyl acetate in hexane to yield 880 mg of the title product as a white solid.

Workup

  1. additionTo a flame-dried flask containing
  2. waitThe resulting yellow solution is left
  3. customThe volatiles are removed
  4. washThe basic aqueous phase is washed with diethyl ether
  5. extractionThe resulting precipitant is repeatedly extracted with dichloromethane (methanol-chloroform co-solvents)
  6. washThe combined dichloromethane extracts are washed once with dilute sodium bicarbonate
  7. customto remove most of the unreacted 4-hydroxycoumarin
  8. dry with materialbrine, dried (magnesium sulfate)
  9. concentrationfinally concentrated under reduced pressure
  10. customchromatographed with 50% to 66% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3ac233ec6d5e4ad5826c3663c6e4102d
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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