Water → HCID 178445699, Verbindung

HRID 500078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500078
[C:1]1(N2C(S(CCC)(=O)=O)=NN=N2)[CH:6]=CC=C[CH:2]=1.[K].C[Si](C)(C)N[Si](C)(C)C.[CH:28]([C@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:32][CH2:31]1)=O.O>COCCOC>[CH:28](/[C@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:32][CH2:31]1)=[CH:2]\[CH2:1][CH3:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6613044HCID 6613044, VerbindungHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 178453955HCID 178453955, Verbindung

Produkt 1

HCID 178445699HCID 178445699, VerbindungAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a mixture of 1-phenyl-5-propylsulfonyl-1H-tetrazole (3.34 g) and anhydrous ethylene glycol dimethyl ether (60 ml) at −60° C. was added 0.5 M hexamethyldisilazane potassium solution (in toluene, 26.6 ml), and the mixture was stirred for 30 minutes. Under the same condition, a solution of t-butyl trans-4-formylcyclohexylcarbamate (3.02 g) in anhydrous ethylene glycol dimethyl ether (15 ml) was added thereto and 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, and 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 1.31 g of t-butyl trans-4-[(E)-1-butenyl]cyclohexyl-carbamate.

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-e71c3a97d6ca4b06b833ce0eae9e06dc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767854B2

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