Tetrahydrofuran → HCID 86640017, compound
Reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.[H-].[Na+].[Br:9][C:10]1[S:14][C:13]([C:15](=O)[CH3:16])=[CH:12][CH:11]=1.C1C[O:21]CC1>>[CH3:5][O:4][C:1](=[O:6])[CH:15]([C:13]1[S:14][C:10]([Br:9])=[CH:11][CH:12]=1)[CH:16]=[O:21]Participants
Procedure
To a solution of dimethyl carbonate (33.67 mL, 400 mmol) in anhydrous THF (200 mL) was added NaH (12.0 g, 300 mmol, 60% dispersion), which was pre-washed with anhydrous hexane. A solution of 1-(5-bromo-thiophen-2-yl)ethanone (20.51 g, 10 mmol) in THF was added dropwise via an additional funnel. The reaction mixture was stirred under nitrogen atmosphere for overnight. The reaction mixture was cooled off with an ice water bath and quenched with water and acidified to pH 3 with 6.0 M HCl. The organic layer was separated from the aqueous layer, which was washed with DCM three times. The combined organic layer was dried over anhydrous Na2SO4 and concentrated, resulting in the product 3-(5-bromo-thiophen-2-yl-3-oxo-propionic acid methyl ester (25.8 g, 98% yield) as dark brown oil. The crude β-ketoester product was relatively pure by analysis of the 1H NMR spectrum. 1H-NMR (CDCl3): δ 7.48 (d, J=4.1 Hz, 1H), 7.13 (d, J=4.1 Hz, 1H), 3.87 (s, 2H), 3.75 (S, 3H).
Workup
- washwas pre-washed with anhydrous hexane
- temperatureThe reaction mixture was cooled off with an ice water bath
- customquenched with water
- customThe organic layer was separated from the aqueous layer, which
- washwas washed with DCM three times
- dry with materialThe combined organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-16e3bd5936d2416991f59b5477a526a0
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998995B2
Reaction notes
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