Potassium Phosphate, Tribasic → (E)-4-Methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one

HRID 1848413노트

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HRID 1848413 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[B-](F)(F)(F)/[CH:10]=[CH:11]/[CH3:12].[K+].FC(F)(F)S(O[C:23]1[C:24]([CH3:33])=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[O:27][CH2:26]2)(=O)=O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:33][C:24]1[C:23](/[CH:10]=[CH:11]/[CH3:12])=[CH:31][CH:30]=[C:29]2[C:25]=1[CH2:26][O:27][C:28]2=[O:32]

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 49761691Potassium trans-1-propenyltrifluoroborateHCID 866472924-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

생성물 1

HCID 86709439(E)-4-Methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To Pd(dppf)Cl2 (0.220 g, 0.338 mmol), K3PO4 (6.75 mL, 1 M in water, 6.75 mmol) in THF (22 mL) was added potassium (E)-trifluoro(prop-1-en-1-yl)borate (0.749 g, 5.06 mmol) and 4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate (I-4B, Method 2, step D, 1.0 g, 3.38 mmol). The reaction mixture was de-gassed for 10 min and the resulting mixture was stirred overnight at 70° C. The reaction mixture was cooled to room temperature and diluted with EtOAc and water. After separation of layers, the aqueous layer was extracted with EtOAc, and combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography using (0-50%) acetone-hexanes as mobile phase to give the title compound. LC/MS: [(M+1)]+=189

후처리

  1. customThe reaction mixture was de-gassed for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with EtOAc and water
  4. customAfter separation of layers
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washwere washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6c459e9137864382bdb94b6ce372bf7e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952166B2

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