Water → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 574059

Reaktionsgleichung

Reaktionsgleichung von HRID 574059
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[Li]CCCC.[OH:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].O>C1COCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:6][CH:7]=1.[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]([OH:25])([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:23]3[CH:22]=[C:21]([OH:20])[CH:34]=[CH:33][CH:32]=3)=[CH:3][CH:4]=2)=[N:12]1

Komponenten

8

Edukt 4

HCID 962WaterHCID 830503-HydroxybenzophenoneHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

Produkt 2

HCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 599879993-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(4-Bromophenyl)-4,4-dimethyl-1,3-oxazoline 1 was prepared as described in Example 4. To a stirred solution of 2-(4-bromophenyl)-4,4-dimethyl-1,3-oxazoline (1.5 g, 6 mM) in anhydrous THF (10 mL) at −78° C. was added slowly n-BuLi (384 mg, 6 mM) in hexane over the period of 20 min. After that the reaction mixture was stirred at −78° C. for another 30 min. To this stirred solution was added 3-hydroxybenzophenone (534 mg, 2.7 mM) dissolved in anhy. THF (10 mL) by dropwise at −78° C. and allowed to stir at room temperature overnight. To this reaction mixture was added 20 mL of water to quench the reaction and extracted with CH2Cl2 (3×50 mL) and the combined extract was dried over anhydrous Mg2SO4. The oily residue obtained on evaporation of the solvent was purified by silica gel column chromatography using hexane/EtOAc (1:1) mixture gave 3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol (2) as colorless crystalline solid. Yield: 0.855 g (85%). Mass: 374 (MH+), 372 (M-H).

Aufarbeitung

  1. dissolutiondissolved in anhy
  2. customdropwise at −78° C.
  3. stirringto stir at room temperature overnight
  4. customto quench
  5. customthe reaction
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. extractionthe combined extract
  8. dry with materialwas dried over anhydrous Mg2SO4
  9. customThe oily residue obtained on evaporation of the solvent
  10. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fed17c506bf24ee89111b30b5c4683f4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034798B2

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