Methane → 2-Indanol

HRID 1646605

Reaktionsgleichung

Reaktionsgleichung von HRID 1646605
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([OH:11])[CH2:6]2.C(=O)([O-])[O-].[Na+].[Na+].C.[PH2]([O-])=O.[Na+]>O.[Pd].O1CCCC1>[CH2:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][CH:2]=2)[CH2:6][CH:5]1[OH:11]

Komponenten

8

Edukt 4

HCID 297MethaneHCID 10340Sodium Carbonate2×HCID 145152994-bromo-2,3-dihydro-1H-inden-2-olHCID 178527019HCID 178527019, Verbindung2×

Produkt 1

HCID 779362-Indanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.0 g of 4-bromo-2-indanol (RS), 60 ml of tetrahydrofuran, 1.6 g of anhydrous sodium carbonate and 0.28 g of palladium at 10% on active charcoal are agitated for 5 minutes. A solution of 1.36 g of sodium hypophosphite in 8 ml of water is introduced over 10 minutes and the whole is taken to 50° C. for 2 hours. 1.60 g of sodium carbonate is added, then at 50° C. 1.36 g of sodium hypophosphite in 8 ml of water is added drop by drop. The mixture is heated for 3 hours, and after cooling it is filtered. The filtrate is rinsed with isopropyl ether, with methanol, and concentrated to dryness under reduced pressure. The residue is taken up in 150 ml of isopropyl ether and 150 ml of water. After decanting, extraction is carried out with isopropyl ether; the extracts are dried and brought to dryness under reduced pressure. The residue is chromatographed on silica in a hexane-ethyl acetate mixture (7-3) and 1.6 g is obtained, M.p.=69° C.

Aufarbeitung

  1. customat 50° C
  2. temperatureThe mixture is heated for 3 hours
  3. temperatureafter cooling it
  4. filtrationis filtered
  5. washThe filtrate is rinsed with isopropyl ether, with methanol
  6. concentrationconcentrated to dryness under reduced pressure
  7. customAfter decanting
  8. extractionextraction
  9. customthe extracts are dried
  10. customThe residue is chromatographed on silica in a hexane-ethyl acetate mixture (7-3)
  11. custom1.6 g is obtained

Quellen und Nachweise

ORD-Eintrag
ord-1a541a954e824e3286d90f0573393aae
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180741

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