Trifluoroacetic acid → 3-(2,4-Dihydroxy-phenyl)-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 61867

반응식

HRID 61867 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C[C:17]([CH3:20])([O-:19])[CH3:18].[Na+].F[B-](F)(F)F.[C:27]([PH+](C(C)(C)C)C(C)(C)C)([CH3:30])(C)[CH3:28].FC(F)(F)C(O)=[O:43].P([O-])([O-])(O)=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)Cl.CO.C1(C)C=CC=CC=1>[OH:43][C:28]1[CH:20]=[C:17]([OH:19])[CH:18]=[CH:30][C:27]=1[CH:8]1[CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]([CH3:13])([CH3:14])[C:9]1=[O:15]

참가 물질

10

반응물 5

HCID 6422Trifluoroacetic acidHCID 24450Potassium Phosphate, DibasicHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2회HCID 23676156Sodium t-butoxide

생성물 1

HCID 668346193-(2,4-Dihydroxy-phenyl)-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one수율 36%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
70 °C

실험 절차

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 10 g), 2-bromo-1,3-dihydroxytetrahydropyranbenzene (Compound Z9, 20.98 g), sodium t-butoxide (5.88 g), palladium acetate (550 mg) and tri-t-butylphosphonium tetrafluoroborate (710 mg), toluene (40 mL) was added and the mixture was stirred and heated at 70° C. under nitrogen atmosphere for 6 hr. After cooling, the reaction mixture was added with methanol (38 mL) and trifluoroacetic acid (14.54 mL) at room temperature, and then stirred at room temperature overnight. To the resulting residues, methylene chloride and saturated dipotassium hydrogen phosphate were added and the organic layer was washed with saturated brine. Thereafter, the organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (5.53 g, 36%).

후처리

  1. temperatureAfter cooling
  2. stirringstirred at room temperature overnight
  3. washthe organic layer was washed with saturated brine
  4. dry with materialThereafter, the organic layer was dried over magnesium sulfate
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0efc1906e96e4b0f843e4ee769e03666
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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