Chlorotrimethylsilane → N-ethoxalyl-2-trimethylsilyloxymethyltetrahydroquinoline

HRID 52487

Reaktionsgleichung

Reaktionsgleichung von HRID 52487
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.C(N(CC)CC)C.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].[C:25](Cl)(=[O:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>ClCCl.O>[C:25]([N:4]1[C:5]2[CH:10]([CH2:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH2:12][CH:3]1[CH2:2][O:1][Si:21]([CH3:23])([CH3:22])[CH3:20])([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:31]

Komponenten

7

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine2×HCID 20884Ethoxalyl chlorideHCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanol

Produkt 1

HCID 67722031N-ethoxalyl-2-trimethylsilyloxymethyltetrahydroquinolineAusbeute 106 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-hydroxymethyltetrahydroquinoline (7.86 g, 48.16 mmol) in dichloromethane (80 mL) containing triethylamine (10 mL, 72.23 mmol) was added trimethylsilyl chloride (6.7 mL, 52.97 mmol) at 0° C. The mixture was stirred for 10 min at 0° C. followed by addition of triethylamine (10 mL) and ethyl chlorooxalate (5.9 mL, 52.97 mmol). The mixture was stirred for 30 min at 0° C. and water was added. The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated to give 15.6 g of N-ethoxalyl-2-trimethylsilyloxymethyltetrahydroquinoline (106%): 1H NMR (270 MHz, CDCl3) δ6.97~7.16 (m, 4H), 4.68 (m, 1H), 4.09 (q, 2H, J=7 Hz), 3.72 (m, 1H), 3.54 (m, 1H), 2.65 (m, 2H), 2.37 (m, 1H), 1.69 (m, 1H), 1.06 (t, 3H, J=7 Hz), 0.03 (s, 9H).

Aufarbeitung

  1. stirringThe mixture was stirred for 30 min at 0° C.
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d945c2c0c67642de846b24ce3050e7a9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616586

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