Boron trifluoride etherate → HCID 54729317, compound

HRID 2293680Notes

Reaction equation

HRID 2293680 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.[CH2:13]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23](O)[CH2:24][CH3:25])[CH:14]=[CH2:15].B(F)(F)F.CCOCC>O1CCOCC1>[CH2:13]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([C:3]1[C:4](=[O:12])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:24][CH3:25])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 21477236HCID 21477236, compoundHCID 546829304-Hydroxycoumarin

Product 1

HCID 54729317HCID 54729317, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flame-dried flask containing a near-solution of 4-hydroxycoumarin (337mg) and 1-(2-allyloxyphenyl)propanol of Preparation 36 (500 mg) in anhydrous dioxane (10 mL) under nitrogen is added boron trifluoride etherate (1.31 mL). The resulting solution is stirred at RT for 25 hrs. concentrated to remove solvent, diluted with aqueous sodium hydroxide (5%, 20 mL) and extracted with methylene chloride (2×25 mL). The organic phase is discarded and the aqueous phase is adjusted to pH 1 using 6M hydrochloric acid and extracted with methylene chloride (2×25 mL). The organic phase is washed with saline (10 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a viscous residue which is then chromatographed on silica gel (230400 mesh, 45g), eluting with a gradient of ethyl acetate/hexane (5/95-10/90). Pooling of fractions having an Rf =0.44 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent gives the title compound.

Workup

  1. additionTo a flame-dried flask containing
  2. concentrationconcentrated
  3. customto remove solvent
  4. additiondiluted with aqueous sodium hydroxide (5%, 20 mL)
  5. extractionextracted with methylene chloride (2×25 mL)
  6. extractionextracted with methylene chloride (2×25 mL)
  7. washThe organic phase is washed with saline (10 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a viscous residue which
  11. customis then chromatographed on silica gel (230400 mesh, 45g)
  12. washeluting with a gradient of ethyl acetate/hexane (5/95-10/90)
  13. customby TLC (ethyl acetate/hexane, 25/75) and removal of solvent

Sources & evidence

ORD record
ord-c8d67c8c272c4dacbe91f37edf2e7d56
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

Loading…