Ethyl Acetate → HCID 71278776, compound

HRID 1749902Notes

Reaction equation

[OH:1][C:2]1[C:10]2[O:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].[C:20]([N:27]1[CH2:32][CH2:31][CH:30](Br)[CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(OCC)(=O)C>CN(C=O)C>[CH3:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[CH2:8][O:9][C:10]=2[C:2]=1[O:1][CH:30]1[CH2:31][CH2:32][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 7-hydroxy-6-methoxybenzofuran-3(2H)-one (0.30 g, 1.7 mmol) in DMF (5.0 mL) was added with potassium carbonate (1.0 g, 7.2 mmol), and N-Boc-4-bromopiperidine (0.50 g, 1.9 mmol), and the mixture was stirred at 80° C. for 12 hours. The reaction mixture was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (1:1)) to obtain tert-butyl 4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yloxy)piperidine-1-carboxylate (0.019 g, 3%).

Workup

washthe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
washthe residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (1:1))

Sources & evidence

ORD record: ord-0d08a82f43ff46a99b8d77964da0d8ba
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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