Cesium carbonate → 1-(4-Benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid ethyl ester
Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:16])[C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:20][C:21]([C:23]1([CH2:26]OS(C)(=O)=O)[CH2:25][CH2:24]1)=[O:22])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:18]([O:20][C:21]([C:23]1([CH2:26][O:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([CH3:17])[C:11]=2[CH3:16])[CH2:25][CH2:24]1)=[O:22])[CH3:19]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
A suspension of 4-benzyloxy-2,3-dimethyl-phenol (960 mg), 1-methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester, prepared as in Step 1 (890 mg) and cesium carbonate (1.5 g) in DMF (20 mL) was stirred at 130 ° C for 6 h, and the mixture was partitioned between EtOAc and water. The organic layer was washed with water, dried over MgSO4 and evaporated. The residue was purified by silica gel column eluting with 10% EtOAc in hexane to give 0.78 g of 1-(4-benzyloxy-2,3-dimethyl-phenoxymethyl)-cyclopropanecarboxylic acid ethyl ester as a clear oil.
Aufarbeitung
- customthe mixture was partitioned between EtOAc and water
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was purified by silica gel column
- washeluting with 10% EtOAc in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-ecfcfc38860642429c18f02ac66cff43
- Quelldatensatz
- uspto-grants-2009_08
- Patentnummer
- US07576094B2
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