(Dimethylamino)trimethylstannane → 4-acetyloxy-3,5-dimethyl-6-(6-dimethylaminobenzofuran-2-yl)-2H-pyran-2-one

HRID 1357212Notes

Reaction equation

[CH3:1][N:2]([Sn](C)(C)C)[CH3:3].[C:8]([O:11][C:12]1[C:17]([CH3:18])=[C:16]([C:19]2[O:20][C:21]3[CH:27]=[C:26](OS(C(F)(F)F)(=O)=O)[CH:25]=[CH:24][C:22]=3[CH:23]=2)[O:15][C:14](=[O:36])[C:13]=1[CH3:37])(=[O:10])[CH3:9]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([O:11][C:12]1[C:17]([CH3:18])=[C:16]([C:19]2[O:20][C:21]3[CH:27]=[C:26]([N:2]([CH3:3])[CH3:1])[CH:25]=[CH:24][C:22]=3[CH:23]=2)[O:15][C:14](=[O:36])[C:13]=1[CH3:37])(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrakis(triphenylphosphine)palladium (3 mg) and dimethylaminotrimethyltin (34 mg) were added to a solution of 4-acetyloxy-3,5-dimethyl-6-(6-(trifluoromethanesulfonyloxy) benzofuran-2-yl)-2H-pyran-2-one (45 mg) in toluene (5 ml), and the mixture was stirred at 50° C. overnight. After cooling, the reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1) to obtain 4-acetyloxy-3,5-dimethyl-6-(6-dimethylaminobenzofuran-2-yl)-2H-pyran-2-one.

Workup

temperatureAfter cooling
concentrationthe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1)

Sources & evidence

ORD record: ord-96a3a9973c4c40018ef7b40f8ef2d6ae
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589984B1

Reaction notes

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