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Hydrochloric Acid → HCID 11451992, Verbindung

HRID 1791031
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1791031
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]=[C:12]1[CH2:18][CH:17]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13]1.[CH2:36](Br)[CH3:37].Cl>O1CCCC1.ClCCl.O>[CH2:36]([C:17]1([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13][C:12](=[CH2:11])[CH2:18]1)[CH3:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 2733832Lithium hexamethyldisilazaneHCID 11439769HCID 11439769, Verbindung

Produkt 1

HCID 11451992HCID 11451992, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.030 ml (1.1 equivalents) of 1,3-dimethylpropyleneurea and then 0.246 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 80 mg (0.22 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 1, in solution in 2.2 ml of tetrahydrofuran. The reaction medium then assumes a dark yellow color. After stirring for 15 minutes, 0.0185 ml (1.1 equivalents) of ethyl bromide is added. After stirring for 5 minutes, water, 1N hydrochloric acid and dichloromethane are added. After separating the organic and aqueous phases, the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed with brine, are dried and are finally concentrated under vacuum. The crude reaction product is then purified by chromatography on silica gel (ethyl acetate/heptane 25/75) to give 56 mg (58%) of methyl 5-ethyl-3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate in the form of an oil; 1H NMR (300 MHz, CDCl3): 0.97 (t, J=7.3 Hz, 3H), 2.41 (q, J=7.3 Hz, 2H), 3.83 (s, 3H), 4.28 (d, J=14.7 Hz, 1H), 4.58 (d, J=14.7 Hz, 1H), 4.86 (s, 1H), 5.02 (s, 1H), 6.82 (d, J=8.5 Hz, 1H), 7.35 (m, 5H), 7.85 (dd, J=8.46 and 2 Hz, 1H), 8.08 (d, J=2.07 Hz, 1H).

Aufarbeitung

  1. customprepared
  2. stirringAfter stirring for 5 minutes
  3. customAfter separating the organic and aqueous phases
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic phases are washed with brine
  6. customare dried
  7. concentrationare finally concentrated under vacuum
  8. customThe crude reaction product
  9. customis then purified by chromatography on silica gel (ethyl acetate/heptane 25/75)

Quellen und Nachweise

ORD-Eintrag
ord-c49d4299a4bd4422926a75399ae58a44
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07071340B2

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