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 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 min. 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 min then heated to 80° C. After a 1 hr 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 min
- customsparged for an additional 10 min
- temperaturethe solution was cooled to <10° C.
- customthen quenched 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-d08f5f4ea647492b9a94ce24b50f968b
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062070B2
Reaction notes
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