Water → 2-methoxy-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one
Reaction equation
C(OC([CH:6]1[C:12](=[O:13])[CH:11](C(OCC)=O)[CH2:10][C:9]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:8]=2[CH2:7]1)=O)C.[OH-].[K+].O>C(O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:8]2[CH2:7][CH2:6][C:12](=[O:13])[CH2:11][CH2:10][C:9]=2[CH:19]=1Participants
Procedure
2-Methoxy-7-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-6,8-dicarboxylic acid diethyl ester (18.2 g, 0.0544 mol) was dissolved in ethanol and the solution was treated with Potassium hydroxide (24.4 g, 0.435 mol) in Water (140 g, 7.6 mol). The reaction was then refluxed until HPLC showed consumption of starting material (˜5 hours). The reaction was then acidified with 1N HCl and the product was extracted with dichloromethane. Organic extracts were dried over sodium sulfate, filtered and reduced. The crude mixture was filtered through a plug of silica rinsing with dichloromethane before purification. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 6.0 grams (58%) of 2-Methoxy-5,6,8,9-tetrahydro-benzocyclohepten-7-one.
Workup
- temperatureThe reaction was then refluxed until HPLC
- customconsumption of starting material (˜5 hours)
- extractionthe product was extracted with dichloromethane
- dry with materialOrganic extracts were dried over sodium sulfate
- filtrationfiltered
- filtrationThe crude mixture was filtered through a plug of silica rinsing with dichloromethane before purification
- customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)
Sources & evidence
- ORD record
- ord-b781a195cae740d2a600b59ce47299bc
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148391B2
Reaction notes
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