1,1-Dibromoethane → 4,4-Dimethyl-2-(4'-tetrahydropyranyloxymethylbiphenyl-2-yl)oxazoline

HRID 744959

Reaktionsgleichung

Reaktionsgleichung von HRID 744959
[Mg].BrC(Br)C.BrC1C=CC(C[C:12]2([O:18][C:19]3([CH2:25][C:26]4[CH:31]=[CH:30][C:29](Br)=[CH:28]C=4)CCCCO3)[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=CC=1.[CH3:35][C:36]1([CH3:49])[CH2:40][O:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2OC)=[N:37]1.[Cl-].[NH4+]>O1CCCC1>[CH3:49][C:36]1([CH3:35])[CH2:40][O:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:30]2[CH:31]=[CH:26][C:25]([CH2:19][O:18][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)=[CH:28][CH:29]=2)=[N:37]1

Komponenten

7

Edukt 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224Magnesium2×HCID 699599014-Bromobenzyl-tetrahydropyranyl ether

Produkt 1

HCID 153808764,4-Dimethyl-2-(4'-tetrahydropyranyloxymethylbiphenyl-2-yl)oxazolineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Tetrahydrofuran (15 ml) was added to 1.2 g (49.4 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, a solution of 11.0 g (40.6 mmol) of 4-bromobenzyl-tetrahydropyranyl ether in tetrahydrofuran (15 ml) was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the resulting mixture was further stirred at room temperature for one hour. Then, a solution of 7.0 g (34.1 mmol) of 4,4-dimethyl-2-(2'-methoxyphenyl)oxazoline in tetrahydrofuran (5 ml) was dropwise added thereto, followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, 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 6.61 g of the title compound as an oil (yield 53%).

Aufarbeitung

  1. customAfter the confirmation of bubbling
  2. stirringthe resulting mixture was further stirred at room temperature for one hour
  3. stirringby stirring for 12 hours
  4. customThe reaction liquid
  5. extractionfollowed by the extraction with chloroform
  6. washAfter washing with water
  7. customdrying
  8. concentrationvacuum concentration
  9. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-2cb36b6669d04e53b88173361e27a691
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559236

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