Benzhydrol → HCID 54711509, compound

HRID 2293659Notes

Reaction equation

HRID 2293659 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.[C:13]1([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>O1CCOCC1.C(OCC)C>[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])[C:3]=1[CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7037BenzhydrolHCID 8000Boron trifluoride etherateHCID 546829304-Hydroxycoumarin

Product 1

HCID 54711509HCID 54711509, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 324 mg of 4-hydroxycoumarin and 368 mg of commercially available diphenylcarbinol in 30 mL of dioxane is added 0.37 mL of boron trifluoride etherate. After 100 hours at room temperature the reaction solution is diluted with 40 mL of diethyl ether and washed with water. The organic phase is dried (magnesium sulfate) and concentrated under reduced pressure. The residue is flash column chromatographed with 20% to 80% ethyl acetate in hexanes to give 587 mg of the title product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed with 20% to 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7b77daa3092b4f0a9ad301f4e83e248d
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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