Diethyl Ether → 4-(2-Phenyl-chroman-6-yloxy)-1-propyl-cyclohexanol

HRID 59778

Reaktionsgleichung

Reaktionsgleichung von HRID 59778
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([Mg]Cl)[CH2:26][CH3:27].C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]4[CH2:23][CH2:22][C:21]([CH2:25][CH2:26][CH3:27])([OH:24])[CH2:20][CH2:19]4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 903901554-(2-Phenyl-chroman-6-yloxy)-cyclohexanoneHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 903900044-(2-Phenyl-chroman-6-yloxy)-1-propyl-cyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

100 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanone were dissolved at room temperature in 5 ml of tetrahydrofuran. A 2M solution of propylmagnesium chloride in diethyl ether (0.31 ml, 2 eq) was added, and stirring at room temperature was continued for 4 h. The reaction was stopped by careful addition of saturated aqueous ammonium chloride solution. The aqueous layer was extracted with methyl tert-butyl ether. The organic layer was dried over sodium sulfate and filtered, and the solvent removed by evaporation. The resulting oil was chromatographed over silica gel using heptane/ethyl acetate 20:1 as the eluent. 54 mg of the title compound were isolated as a pale yellow oil (48%).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with methyl tert-butyl ether
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. customThe resulting oil was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-81069c4c704e42ddb46130f780f09869
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440941B2

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