Water → HCID 178444561, Verbindung

HRID 500082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500082
[CH2:1](S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O)[CH3:2].C[Si](C)(C)N[Si](C)(C)C.[K].[CH:27]([CH2:29][CH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)=O.O>COCCOC>[CH2:30]([C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)[CH2:29]/[CH:27]=[CH:1]/[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7536625-Ethylsulfonyl-1-phenyl-1H-tetrazoleHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 178453885HCID 178453885, Verbindung

Produkt 1

HCID 178444561HCID 178444561, VerbindungAusbeute 9,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a mixture of 5-ethylsulfonyl-1-phenyl-1H-tetrazole (5.0 g) and anhydrous ethylene glycol dimethyl ether (50 ml) at −60° C. was added 0.5 M potassium hexamethyldisilazane solution (in toluene, 19.7 ml), and the mixture was stirred for 20 minutes. Under the same condition, a solution of t-butyl trans-4-(2-formylethyl)cyclohexylcarbamate (2.65 g) (Example 73 (3)) in anhydrous ethylene glycol dimethyl ether (20 ml) was added thereto. The reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added water, and the mixture was stirred for 1 hour, then extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 252 mg of t-butyl trans-4-[(E)-3-pentenyl]cyclohexylcarbamate.

Aufarbeitung

  1. stirringstirred overnight
  2. stirringthe mixture was stirred for 1 hour
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bab4c500ebb74311b1bd2fc309cf5833
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767854B2

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