Fenipentol → 4-Hydroxy-3-(1-phenylpentyl)-coumarin

HRID 2293664Notes

Reaction equation

HRID 2293664 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](O)[CH2:20][CH2:21][CH2:22][CH3:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>O1CCOCC1>[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:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 3338FenipentolHCID 8000Boron trifluoride etherateHCID 546829304-Hydroxycoumarin

Product 1

HCID 547115384-Hydroxy-3-(1-phenylpentyl)-coumarinYield 12.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flame-dried flask containing a mixture of 811 mg of 4-hydroxycoumarin and 985 mg of 1-phenyl-1-pentanol in 30 mL of dioxane under an argon atmosphere is added 3.0 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, 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 adsorbed onto silica and flash column chromatographed with 40% to 50% ethyl acetate in hexane to yield 193 mg of the title product as white crystals.

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 40% to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-16ded8bc12c74b9cae200ee95350101d
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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