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

HRID 1429285
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HRID 1429285 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 6093782Bis(acetonitrile)dichloropalladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7b8c0c05149041d3a41e305430422825
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940184B2

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