Diiodomethane → HCID 67191093, Verbindung

HRID 2191158

Reaktionsgleichung

Reaktionsgleichung von HRID 2191158
[CH2:1]([Zn]CC)[CH3:2].[CH3:6]CCCCC.F[C:13](F)(F)[C:14]([OH:16])=[O:15].ICI.C=[C:23]([CH2:37]CC)[CH2:24][CH2:25][CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])C(OCC)=O>ClCCl>[CH2:1]([O:16][C:14]([CH2:13][CH2:6][C:24]1([CH2:25][CH2:26][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:23][CH2:37]1)=[O:15])[CH3:2]

Komponenten

6

Edukt 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 86634462Diethyl 4-methyleneheptanedicarboxylateHCID 178443585HCID 178443585, Verbindung

Produkt 1

HCID 67191093HCID 67191093, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

24.5 ml (24.5 mmol) of 1.0 M diethyl zinc/hexane solution was added to 30 ml of dichloromethane, and then a solution of 1.89 ml (24.5 mmol) of trifluoroacetic acid in 10 ml of dichloromethane was added with stirring under ice-cooling. The reaction solution was stirred for 20 minutes at the same temperature, then a solution of 1.97 ml (24.5 mmol) of diiodomethane in 10 ml of dichloromethane was added and stirred for 20 minutes, and 1.40 g (6.13 mmol) of a solution of diethyl 4-methyleneheptanedicarboxylate (compound described in J.A.C.S. 107, 13, 3981-3997 (1985)) in 10 ml of dichloromethane was further added. After the reaction solution was stirred for 6 hours at room temperature, ice water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=5:1) to give 1.48 g of the title compound as a brown oil (yield: 99%).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe reaction solution was stirred for 20 minutes at the same temperature
  3. stirringstirred for 20 minutes
  4. stirringAfter the reaction solution was stirred for 6 hours at room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationfollowed by concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c6e363e9d304ceba1d7a702878934bb
Quelldatensatz
uspto-grants-2012_12
Patentnummer
USRE043858E1

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