3,4,5,6-Tetrahydrophthalic anhydride → HCID 69312050, compound
Reaction equation
[Br-].[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH3:10])[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[C:36]1(=[O:46])[C:44]2[CH2:43][CH2:42][CH2:41][CH2:40][C:39]=2[C:38](=O)[O:37]1>O1CCCC1>[Br:2][C:3]1[CH:4]=[C:5]([C:9](=[C:38]2[C:39]3[CH2:40][CH2:41][CH2:42][CH2:43][C:44]=3[C:36](=[O:46])[O:37]2)[CH3:10])[CH:6]=[CH:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of EXAMPLE 285B (1.88 g, 3.4 mmol) in tetrahydrofuran (100 ml) was treated with potassium t-butoxide (1N solution in tetrahydrofuran, 3.4 ml, 3.4 mmol) at −78° C. for 1 hour, and was allowed to warm up to 0° C. over 30 minutes. A solution of 4,5,6,7-tetrahydroisobenzofuran-1,3-dione (0.54 g, 3.4 mmol) in tetrahydrofuran (10 ml) was then added. The reaction mixture was warmed up to room temperature, and stirred at room temperature for additional 4 hours. After quenching with water, the reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine, and concentrated. The residue was separated by flash chromatography (20% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 320 (M+H)+.
Workup
- temperatureThe reaction mixture was warmed up to room temperature
- customAfter quenching with water
- customthe reaction mixture was partitioned between ethyl acetate and brine
- washThe organic phase was washed with brine
- concentrationconcentrated
- customThe residue was separated by flash chromatography (20% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-668219fa247942afa0f5cf40ce3f66cf
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09283222B2
Reaction notes
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