StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Ethylbenzene → HCID 23497591, Verbindung

HRID 397468
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 397468
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.C(C1C=CC=CC=1)C.[C:37]1([S:43]([O:46][C:47]2[CH:48]=[CH:49][C:50]([CH2:53]Br)=[N:51][CH:52]=2)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1.CCOCC.CCCCCC>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH:9]([CH2:53][C:50]2[CH:49]=[CH:48][C:47]([O:46][S:43]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)(=[O:45])=[O:44])=[CH:52][N:51]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7500EthylbenzeneHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 2724682Lithium diisopropylamideHCID 10639974HCID 10639974, Verbindung

Produkt 1

HCID 23497591HCID 23497591, VerbindungAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×
HCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

A solution of ethyl N-(diphenylmethylene)glycinate (1.71 g, 6.40 mmol) in dry THF (10 ml) was added to a stirrred solution of LDA (2M in heptane/TNF/ethylbenzene, 320 ml, 6.40 mmol) in dry THF 910 ml) at −70° under nitrogen. After stirring at this temperture for 0.75 h, a solution of 5-benzenesulphonyloxy-2-bromomethylpyridine (2.00 g, 6.01 mmol); [prepared as described by Myers et al, J.O.C. 61, 813 (1996)] in dry THF (10 ml) was added. The reaction mixture was stirred at −70° for 1 h then at room temperature for 18 h. The reaction was quenched with water 910 ml) then partitioned between EtOAc (70 ml) and bring (30 ml). The phases were separated and the aqueous phase re-extracted with EtOAc (2×40 ml). The combined organic extracts were washed with brine (10 ml), dried (Na2SO4) and evaporated in vacuo to afford the crude product as a dark oil. Chromatography (silica: 60-75% Et2O/Hexane) afforded the title compound as a tan-coloured solid (2.25 g, 72%). δH (CDCl3) 8.02 (1H, d, J 2.8 Hz), 7.72 (2H, d, J 8.0 hz), 7.59 (1H, t, J 8.0 hz), 7.50 (2H, dd, J 8.4 Hz), 7.40-7.27 (8H, m), 7.19 (1H, dd, J 8.5, 2.8 Hz), 7.11 (1H, d, J 8.5 Hz), 6.67 (2H, br d, J 8.0 Hz), 4.50 (1H, dd, J 9.0, 4.6 Hz), 4.25-4.10 (2H, m), 3.50-3.33 (2H, m) and 1.24 (3H, t, J 7.2 Hz), m/z (ES+, 70V) 515 (MH+).

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction mixture was stirred at −70° for 1 h
  3. waitat room temperature for 18 h
  4. customThe reaction was quenched with water 910 ml)
  5. customthen partitioned between EtOAc (70 ml)
  6. customThe phases were separated
  7. extractionthe aqueous phase re-extracted with EtOAc (2×40 ml)
  8. washThe combined organic extracts were washed with brine (10 ml)
  9. dry with materialdried (Na2SO4)
  10. customevaporated in vacuo
  11. customto afford the crude product as a dark oil

Quellen und Nachweise

ORD-Eintrag
ord-a59c2ea57b5147dab26ce4f7b81d8e7e
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610700B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion