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

HRID 1848413ノート

反応式

HRID 1848413 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
70 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-6c459e9137864382bdb94b6ce372bf7e
出典データセット
uspto-grants-2015_02
特許番号
US08952166B2

反応ノート

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