Butyl vinyl ether → 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one
Reaction equation
[CH3:1][C:2]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:19].[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:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:19])[O:5][CH2:4]2)=[CH2:21])[CH2:24][CH2:25][CH3:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a 1 L 3-neck flask 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)) 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 sparged for an additional 10 minutes then heated to 80° C. After a 1 hour age, the solution was cooled to <10° C., then quenched with 630 mL EtOAc and washed with 5% NH4Cl (2×315 mL), 10% brine (2×315 mL), 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
- customThe solution was sparged with N2 for 20 minutes
- customsparged for an additional 10 minutes
- temperaturethe solution was cooled to <10° C.
- customquenched with 630 mL EtOAc
- washwashed with 5% NH4Cl (2×315 mL), 10% brine (2×315 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
- customflushed with EtOAc (3×100 mL)
- customto remove excess butyl vinyl ether
Sources & evidence
- ORD record
- ord-2b779a7d6ec64f5db74cc0572f0701e8
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139585B2
Reaction notes
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