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Ethyl isobutyrate → 2,2-Dimethyl-3-[4-(3-pyridylmethyl)phenyl]propionic acid ethyl ester

HRID 1680027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1680027
[CH:1]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.C(OCC)(=O)C(C)C.[CH2:29]([O:31][C:32](=[O:50])/[C:33](/[CH2:48]C)=[CH:34]/[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:37][CH:36]=1)[CH3:30].[Cl-].[NH4+]>O1CCCC1.CCCCCC.CN(P(N(C)C)(N(C)C)=O)C>[CH2:29]([O:31][C:32](=[O:50])[C:33]([CH3:48])([CH3:1])[CH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH2:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:39][CH:40]=1)[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 6

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 12904571(E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl esterHCID 178418339Butyllithium

Produkt 1

HCID 54391330
2,2-Dimethyl-3-[4-(3-pyridylmethyl)phenyl]propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a 3.0 M solution of lithium diisopropylamide in tetrahydrofuran [prepared from diisopropylamine (0.56 ml), tetrahydrofuran (5 ml) and a 1.4 M solution of butyllithium in hexane (2.2 ml)] was added dropwise 0.41 ml of ethyl isobutyrate at -70° C., and the mixture was stirred at that temperature for 40 minutes. To it was added dropwise a solution of 0.26 g of the benzyl chloride compound (prepared as described in Reference Example 2) in 2.8 ml of a mixture of HMPA and tetrahydrofuran (1:1) at -70° C., and the mixture was stirred at that temperature for 2 hours, and then at room temperature for one hour. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 0.27 g of the title compound having the following physical characteristics:

Aufarbeitung

  1. stirringthe mixture was stirred at that temperature for 2 hours
  2. waitat room temperature for one hour
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c926500ccd484dbc938445013593a5c8
Quelldatensatz
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04271170

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