Diethyl Oxalate → Ethyl 2-oxo-2-(10-oxotricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)acetate

HRID 1967178

Reaktionsgleichung

Reaktionsgleichung von HRID 1967178
ClC1C=C(Cl)C=CC=1N1N=C(C(O)=O)C2C3CCC(C4C3=CC=CC=4)C1=2.[CH:27]12[CH2:39][CH2:38][CH:34]([C:35](=[O:37])[CH2:36]1)[C:33]1[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=1.C[Si](C)(C)N[Si](C)(C)C.[Li]CCCC.[C:54](OCC)(=[O:60])[C:55]([O:57][CH2:58][CH3:59])=[O:56]>>[O:60]=[C:54]([CH:36]1[C:35](=[O:37])[CH:34]2[CH2:38][CH2:39][CH:27]1[C:28]1[C:33]2=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:55]([O:57][CH2:58][CH3:59])=[O:56]

Komponenten

6

Edukt 5

HCID 7268Diethyl OxalateHCID 13838HexamethyldisilazaneHCID 5825961,4-Ethanonaphthalen-2(1H)-one, 3,4-dihydro-HCID 8662333710-(2,4-Dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxylic acidHCID 178418339Butyllithium

Produkt 1

HCID 67029310Ethyl 2-oxo-2-(10-oxotricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)acetate

Versuchsvorschrift

The title product was prepared by a procedure similar to that described for step 1 of intermediate 1. From tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-one [prepared by one of the methods available in the art of organic synthesis, e.g., as described in Hales et. al. Tetrahedron, 1995, 51, 7777-7790] (2.5 g, 14.53 mmol), hexamethyldisilazane (4.9 ml, 23.2 mmol), 2.34M n-BuLi (10 ml, 23.4 mmol) and diethyl oxalate (3.18 ml, 21.18 mmol) the desired product was obtained (2.3 g, 63%).

Aufarbeitung

  1. customThe title product was prepared by a procedure similar to
  2. customwas obtained (2.3 g, 63%)

Quellen und Nachweise

ORD-Eintrag
ord-51c3c5e8720f485f9bc2c50725805891
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420689B2

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