Hydrochloric Acid → methyl (2S)-5-acetyl-2-ethyl-2,3-dihydro-benzofuran-2-carboxylate
Reaction equation
[CH2:1]([C@@:3]1([C:12]([O:14][CH3:15])=[O:13])[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1)[CH3:2].[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[C:16]([C:9]1[CH:10]=[CH:11][C:5]2[O:4][C@:3]([CH2:1][CH3:2])([C:12]([O:14][CH3:15])=[O:13])[CH2:7][C:6]=2[CH:8]=1)(=[O:18])[CH3:17]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Methyl (2S)-2-ethyl-2,3-dihydro-benzofuran-2-carboxylate(3.1 g, 15 mmol) was mixed with acetyl chloride (3.5 g, 45 mmol) and aluminum chloride (6.0 g, 45 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at 25° C. for 1 hr and then poured into 1 N aqueous HCl (100 mL). The organic layer was separated and the aqueous phase was extracted with dichloromethane (50 mL). The combined extracts were washed with brine and concentrated to give essentially pure methyl (2S)-5-acetyl-2-ethyl-2,3-dihydro-benzofuran-2-carboxylate.
Workup
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with dichloromethane (50 mL)
- washThe combined extracts were washed with brine
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9b23772e317e4423b1d79e6132b6e91c
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524882B2
Reaction notes
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