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

HRID 1848413Notes

Reaction equation

HRID 1848413 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-6c459e9137864382bdb94b6ce372bf7e
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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