Sodium Carbonate → 5-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 2063788Notes

Reaction equation

C(B1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])(C)[O:4]1)=C.C(=O)([O-])[O-].[Na+].[Na+].[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2OC(C)(C)[C:24](=O)[C:23]=2[C:30]=1Br>C(OCC)(=O)C.O.COCCOC.C(O)C>[NH2:18][C:19]1[C:20]([CH3:33])=[C:21]([CH3:32])[C:22]2[O:7][C:6]([CH3:8])([CH3:9])[C:5](=[O:4])[C:11]=2[C:30]=1[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 100 °C

Procedure

2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan (3.79 g, 24.6 mmol), tetrakistriphenyl phosphine palladium (605 mg, 0.523 mmol), sodium carbonate (1.36 g, 12.8 mmol), water (8 mL) and ethanol (5 mL) were added to a solution of DME (14 mL) containing 5-amino-4-bromo-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (2.00 g, 7.04 mmol) synthesized in Reference Example 21, and the mixture was stirred under argon atmosphere at 100° C. for 45 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15) to give 1.47 g of the title compound (yield: 91%).

Workup

customsynthesized in Reference Example 21
temperatureAfter cooled to room temperature
customIt was dried
customAfter that, the solvent was removed under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 98:2 to 85:15)

Sources & evidence

ORD record: ord-e0e50aecc7e7477db5b5cb7b36e6d9db
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288390B2

Reaction notes

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