Sodium borohydride → 4-(2-Phenyl-chroman-6-yloxy)-cyclohexanol

HRID 59779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59779
[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.[BH4-].[Na+]>C(O)C>[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][CH:21]([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

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 903901554-(2-Phenyl-chroman-6-yloxy)-cyclohexanone

Produkt 1

HCID 903899804-(2-Phenyl-chroman-6-yloxy)-cyclohexanolAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

500 mg of 4-(2-phenyl-chroman-6-yloxy)-cyclohexanone (1.6 mmol) were dissolved at 0° C. in 2.5 ml of ethanol. 30 mg of sodium borohydride (0.78 mmol) were added in portions, and stirring at room temperature was continued for 2 h. The solvent was removed under reduced pressure and the residue separated between saturated aqueous sodium hydrogencarbonate solution and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and filtered, and volatile components removed under reduced pressure. 500 mg of the title compound were obtained as a pale yellow solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue separated between saturated aqueous sodium hydrogencarbonate solution and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. customvolatile components removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bad77bf8f38c4ed28ed07e45a81f81f7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440941B2

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