Ethyl bromoacetate → HCID 90417137, Verbindung

HRID 1748398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748398
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH:12]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 90417479HCID 90417479, Verbindung

Produkt 1

HCID 90417137HCID 90417137, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 7-((3-chlorobenzyl)oxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (34 g, 0.09 mol) in THF (50.09 mL) was added a solution of lithium bis(trimethylsilyl)amide (1.06 M in THF, 99.24 mL, 0.11 mol) at −78° C. The reaction was stirred at that temperature for 30 minutes after which ethyl bromoacetate (9.70 mL, 0.09 mol) was added. The reaction was allowed to warm to ambient temperature, stirred overnight and quenched into water (250 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with brine and dried over MgSO4. The organics were concentrated under reduced pressure to afford a yellow-brown oil and carried on crude to the next step. 1H NMR (400 MHz, CDCl3) δ 7.35 (s, 1H), 7.27-7.22 (m, 3H), 7.02 (d, J=8.4 Hz, 1H), 6.59 (dd, J=8.3, 2.5 Hz, 1H), 6.49 (d, J=2.4 Hz, 1H), 4.95 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 3.06-2.91 (m, 1H), 2.87-2.70 (m, 2H), 2.60 (d, J=7.5 Hz, 1H), 2.37 (d, J=8.9 Hz, 1H), 1.54-1.44 (m, 9H), 1.26-1.19 (m, 3H). [M+H]=374.2.

Aufarbeitung

  1. additionwas added
  2. customquenched into water (250 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe organics were concentrated under reduced pressure
  7. customto afford a yellow-brown oil

Quellen und Nachweise

ORD-Eintrag
ord-1da557ebda844af49671f7478efe817a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150572B2

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