Methyl 2-hydroxy-3-propionylbenzoate → Methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate

HRID 1452314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452314
[OH:1][C:2]1[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:16]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C1C=CN=CC=1.ClCCl>[CH:16]1([C:23]([O:1][C:2]2[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

5

Edukt 2

HCID 10899812Methyl 2-hydroxy-3-propionylbenzoateHCID 12556870Cycloheptanecarbonyl chloride

Produkt 1

HCID 19972577Methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture, of 7.3 g of methyl 2-hydroxy-3-propionylbenzoate, 4.7 g of 4-dimethylaminopyridine and 50 ml of dichloromethane was stirred at room temperature. Cycloheptanecarbonyl chloride, 56 g, in 10 ml of dichloromethane, (prepared as described in P. W. Collins et al., J. Med. Chem. 32, 1001-1006 (1989)) was added to the solution using dropwise addition. The mixture was stirred at room temperature for 5 hours and allowed to stand overnight. The reaction mixture was washed, in succession, with 3% hydrochloric acid, saturated aqueous sodium bicarbonate solution and water. This was followed by drying over anhydrous sodium sulfate and evaporation to dryness to provide 9.8 g of crude methyl 2-cycloheptanecarbonyloxy-3-propionylbenzoate. This product was utilized without further purification.

Aufarbeitung

  1. additionwas added to the solution
  2. additionaddition
  3. waitto stand overnight
  4. washThe reaction mixture was washed, in succession, with 3% hydrochloric acid, saturated aqueous sodium bicarbonate solution and water
  5. dry with materialby drying over anhydrous sodium sulfate and evaporation to dryness

Quellen und Nachweise

ORD-Eintrag
ord-902be35490e84e1abd21a94220bdf706
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05605896

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