Acetone Cyanohydrin → HCID 178504767, Verbindung

HRID 24293

Reaktionsgleichung

Reaktionsgleichung von HRID 24293
[CH2:1]=[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[O:3]1.C(N(CC)CC)C.CC(C)(O)C#N.[CH3:24][S:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[C:30]([N+:37]([O-:39])=[O:38])[CH:29]=1)(=[O:27])=[O:26]>C(#N)C.C(OCC)(=O)C>[OH:3][C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[C:1]=1[C:32](=[O:33])[C:31]1[CH:35]=[CH:36][C:28]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:29][C:30]=1[N+:37]([O-:39])=[O:38]

Komponenten

7

Edukt 4

HCID 6406Acetone Cyanohydrin2×HCID 8471TriethylamineHCID 129939774-Methylene-3-oxabicyclo[3.2.1]octan-2-oneHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chloride

Produkt 1

HCID 178504767HCID 178504767, VerbindungAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.76 g (0.02 mol) of 93% 4-methylene-3-oxabicyclo[3.2.1]octan-2-one and 4.45 g (0.044 mmol) of triethylamine are stirred for 6 hours at a temperature of 20° C. in 50 ml of acetonitrile in the presence of 170 mg (2 mmol) of acetone cyanohydrin. 4.22 g (0.16 mol) of 4-methanesulfonyl-2-nitrobenzoyl chloride are then introduced and stirring is continued for a further 12 hours at a temperature of 20° C. A further 170 mg (2 mmol) of acetone cyano-hydrin are then added and stirring is continued for a further 30 minutes until conversion is complete. The reaction mixture is then taken up in ethyl acetate and extracted at a pH value of 13 against water. The aqueous phase is acidifed and extracted with fresh ethyl acetate, once at pH 5 and once at pH 4, dried and concentrated by evaporation. 3.05 g of 4-hydroxy-3-(4-methanesulfonyl-2-nitrobenzoyl)-bicyclo[3.2.1]oct-3-en-2-one with a good level of purity are obtained. The yield is 44.9% based on the starting material 4-methylene-3-oxa-bicyclo[3.2.1]octan-2-one or 52.2% based on the starting material 4-methanesulfonyl-2-nitrobenzoic acid.

Aufarbeitung

  1. stirringstirring
  2. waitis continued for a further 30 minutes until conversion
  3. extractionextracted at a pH value of 13 against water
  4. extractionextracted with fresh ethyl acetate, once at pH 5 and once at pH 4
  5. customdried
  6. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-bdcd0a5f1d9b4a52a5aeb75863e03592
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855831B2

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