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Acetic Acid → Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-1-oxo-2-indancarboxylate

HRID 2268456
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268456
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:48](OCC)=[O:49])([CH2:32][C:33]2[C:38](Br)=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=2[O:46][CH3:47])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>C(OCC)C.C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:32][C:33]3[C:38](=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=3[O:46][CH3:47])[C:48]2=[O:49])=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8058HexaneHCID 18348651Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionateHCID 178418339Butyllithium

Produkt 1

HCID 18348626Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-1-oxo-2-indancarboxylateAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A hexane solution of n-butyl lithium (1.68 M, 11.3 ml, 19.0 mmols) was dropwise added to a THF (100 ml) solution of ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionate (10.0 g, 15.8 mmols), under a nitrogen stream at −90° C or lower. The reaction mixture was stirred for 30 minutes, and a THF (10 ml) solution of acetic acid (1.86 g, 31.6 mmols) was dropwise added thereto still at −90° C. or lower. The reaction mixture was allowed to warm to room temperature, and diluted with diethyl ether. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to obtain the entitled compound (3.78 g) as an oil.

Aufarbeitung

  1. customstill at −90° C.
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution, water
  3. dry with materiala saturated aqueous sodium chloride solution, and then dried
  4. customThe solvent was evaporated out in vacuo
  5. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-35899d0b04194576bd07d2dbee129f8f
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

Notizen zur Reaktion

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