Ethyl Acetate → [2-[4-(Tetradecyloxy)phenyl]ethyl]aminobenzenemethanol

HRID 653792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653792
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)C(OCC)=O)=O)=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:43](OCC)(=[O:45])C.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.O1CCCC1>[CH2:7]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:31][C:32]2[CH:42]=[CH:41][CH:40]=[CH:34][C:33]=2[CH2:43][OH:45])=[CH:26][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 15030160Ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 86745967[2-[4-(Tetradecyloxy)phenyl]ethyl]aminobenzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 42.36 ml of 1 molar lithium aluminum hydride in ether is added dropwise under argon over 20 minutes a solution of ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate in 50 ml of ether and 50 ml of tetrahydrofuran. The mixture is refluxed for 3 hours, cooled to 0° C. and ethyl acetate added. Saturated sodium sulfate is added followed by ether. The mixture is filtered and the cake washed with ether. The filtrate is evaporated and the residue chromatographed on silica gel using 9:1 chloroform:ethyl acetate. The product fractions are combined and evaporated to a residue which is crystallized from hexane to give 4.5 g of the desired product as a white solid, m.p. 67°-70° C.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 3 hours
  2. filtrationThe mixture is filtered
  3. washthe cake washed with ether
  4. customThe filtrate is evaporated
  5. customthe residue chromatographed on silica gel using 9:1 chloroform
  6. customevaporated to a residue which
  7. customis crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-a307d95270954175b42259dc9a7ed31b
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128351

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