Hydrochloric Acid → 7-(3-Hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one

HRID 1429285Notes

Reaction equation

HRID 1429285 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1)(=O)=O.[C:28]([OH:31])#[C:29][CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl>O1CCOCC1.CC#N.CC#N.Cl[Pd]Cl.O>[OH:31][CH2:28][C:29]#[C:30][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 6432594Prop-1-yn-1-olHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 866570063-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate

Product 1

HCID 584024147-(3-Hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6.90 g (17.2 mmol) of 3-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate, 1.5 ml (25.4 mmol) of propyn-1-ol, 12.0 g (36.8 mmol) of caesium carbonate, 150 mg (0.578 mmol) of bis(acetonitrile)palladium(II) chloride and 800 mg (1.68 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl are left to stir at 60° C. for 3 h in 100 ml of dioxane, added to 400 ml of water and acidified using 2 N hydrochloric acid. The aqueous phase is extracted three times with ethyl acetate, and the combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with toluene/ethyl acetate (4:1). Crystallisation of the crude product from toluene/ethyl acetate (10:1) gives 7-(3-hydroxyprop-1-ynyl)-3-(4-methoxyphenyl)chromen-2-one as yellow crystals.

Workup

  1. extractionThe aqueous phase is extracted three times with ethyl acetate
  2. washphases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. filtrationthe residue is filtered through silica gel with toluene/ethyl acetate (4:1)
  6. customCrystallisation of the crude product from toluene/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-7b8c0c05149041d3a41e305430422825
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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