Tetrahydrofuran → 6-ethyl-3H-isobenzofuran-1-one
Reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:20]1COC[CH2:21]1>O>[CH2:20]([C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[CH3:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 6-bromo-3H-isobenzofuran-1-one (Intermediate 72, 0.7 g) and potassium phosphate (1.9 g) in THF (7.3 ml) and water (3.7 ml) was degassed and palladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.3 ml) were added. The resultant mixture was stirred and heated at 100° C. for 1.5 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water and brine then dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give 6-ethyl-3H-isobenzofuran-1-one (0.435 g) as a colourless oil.
Workup
- customwas degassed
- additionpalladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.3 ml) were added
- temperatureAfter cooling to room temperature
- additionthe mixture was diluted with ethyl acetate
- washwashed with water and brine
- dry with materialthen dried (Na2SO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was purified by chromatography on silica
- washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%
Sources & evidence
- ORD record
- ord-607e5955e3fe4e2ab01f9e944a3bfbcf
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067905B2
Reaction notes
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