Triethylamine → (1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

HRID 407864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407864
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:25](=[O:26])[CH:24]2[CH:19]([CH:20]3[O:27][CH:23]2[CH2:22][CH2:21]3)[C:18]1=[O:28].C(N(CC)CC)C>ClCCl>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:26][C:25]1[CH:24]2[CH:19]([C:18](=[O:28])[C:17]=1[C:10]1[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8])[CH:20]1[O:27][CH:23]2[CH2:22][CH2:21]1)=[O:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67284407(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione

Produkt 1

HCID 67284916(1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

A solution of pivaloyl chloride (0.055 g, 0.57 mmol) in dichloromethane (2 ml) is added dropwise to a solution of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione (0.12 g, 0.42 mmol) in dichloromethane (2 ml) at room temperature and the reaction mixture is stirred for 2 minutes. A solution of triethylamine (0.08 ml) in dichloromethane (1 ml) is added and the reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with dichloromethane (20 ml) and washed with saturated aqueous sodium bicarbonate solution. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to give (1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate as a colourless oil.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at room temperature for 3 hours
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-639ec45650af4875a545357d0ad21e8b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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