Water → 4,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

HRID 53426

Reaktionsgleichung

Reaktionsgleichung von HRID 53426
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:28])[CH2:12][O:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[CH:21][CH:20]=2)=[N:9]1.O>O1CCCC1>[CH3:7][C:8]1([CH3:28])[CH2:12][O:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[CH:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=2)=[N:9]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 15289161HCID 15289161, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazolineAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.28 g (38.7 mmol) of aluminum lithium hydride was suspended in tetrahydrofuran (20 ml). At room temperature, 5.0 g (16.9 mmol) of 4,4-dimethyl-2-(4'-carboxybiphenyl-2-yl)oxazoline was gradually added thereto, followed by stirring for 2 hours. After the reaction liquid was cooled with ice, 100 ml of water was added thereto to conduct hydrolysis, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 4.2 g of the title compound (yield 88%).

Aufarbeitung

  1. customAfter the reaction liquid
  2. additionwas added
  3. customhydrolysis
  4. extractionfollowed by the extraction with chloroform
  5. washAfter washing with water
  6. customdrying
  7. concentrationvacuum concentration
  8. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-48167aaa38ef429aba6fe470063ead91
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618969

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