1,1-Dibromoethane → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol

HRID 1756015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756015
[Mg].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1.BrC(Br)C.[CH2:22]1[O:24][CH2:23]1.O1CCCC1>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:22][CH2:23][OH:24])=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 112011,1-DibromoethaneHCID 5462224MagnesiumHCID 133067582-(4-bromophenethoxy)tetrahydro-2H-pyranHCID 21868110Ethylene oxide tetrahydrofuran

Produkt 1

HCID 542369074-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcoholAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Magnesium (1.31 g, 53.90 mmol) was added to a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)bromobenzene (14.00 g, 49.09 mmol) in tetrahydrofuran (20 ml). Then dibromoethane (0.1 ml) was added under an atmosphere of nitrogen gas, and the mixture was stirred under room temperature for 1 hour. After cooling to ice-cooling temperature, 2M-ethylene oxide/tetrahydrofuran solution (49.09 ml, 98.18 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Then, water (40 ml) was added to the reaction mixture. The mixture was extracted with ethyl ether and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2) to give the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol (6.00 g, 42%).

Aufarbeitung

  1. temperatureAfter cooling to ice-
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe mixture was extracted with ethyl ether
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2)

Quellen und Nachweise

ORD-Eintrag
ord-792cb5ff81a8446bb4a470c2632fe0f4
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439911

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