Butyl vinyl ether → 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one

HRID 515109Notes

Reaction equation

HRID 515109 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:17])=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[O:11][CH2:10]2)(=O)=O.[CH:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH2:21].CCN(CC)CC.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH2:23]([O:22][C:20]([C:7]1[C:8]([CH3:17])=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[O:11][CH2:10]2)=[CH2:21])[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 866472924-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate

Product 1

HCID 675169525-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 1 L 3-neck was charged trifluoromethanesulfonic acid, 4-methyl-1-oxo-1,3-dihydro-isobenzofuran-5-yl ester (63.0 g, 213 mmol), DMF (315 mL), butyl vinyl ether (138 mL, 1063 mmol)), and then Et3N (35.6 mL, 255 mmol). The solution was sparged with N2 for 20 minutes. To the solution was added Pd(OAc)2 (1.19 g, 5.32 mmol) and DPPP (2.41 g, 5.85 mmol), and the solution was then sparged for an additional 10 minutes, and then heated to 80° C. After a 1 hour age, the solution was cooled to <10° C., quenched with 630 mL EtOAc, and then washed with 5% NH4Cl (2×315 mL) and 10% brine (2×315 mL). The solution was then dried over MgSO4, filtered, concentrated by rotary evaporation and flushed with EtOAc (3×100 mL) to remove excess butyl vinyl ether, providing crude 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one.

Workup

  1. customThe solution was sparged with N2 for 20 minutes
  2. customthe solution was then sparged for an additional 10 minutes
  3. temperaturethe solution was cooled to <10° C.
  4. customquenched with 630 mL EtOAc
  5. washwashed with 5% NH4Cl (2×315 mL) and 10% brine (2×315 mL)
  6. dry with materialThe solution was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customflushed with EtOAc (3×100 mL)
  10. customto remove excess butyl vinyl ether

Sources & evidence

ORD record
ord-ba6e3a4feeec4d50bf0baec04a12c40e
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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