Water → HCID 12765392, Verbindung

HRID 235078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235078
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[BH4-].[Na+].O>C(O)C.C1(C)C=CC=CC=1.C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH2:7][CH:8]=[CH:9]2

Komponenten

8

Edukt 3

HCID 962WaterHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 4311764Sodium borohydride

Produkt 1

HCID 12765392HCID 12765392, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5.01 g (24.3 mmol) of 6,7-dimethoxy-1-tetralone (Aldrich Chemical Co.) in 100 mL of ethanol was added 0.932 g (24.6 mmol) of NaBH4, and the mixture was stirred for 14 hours at room temperature. Most of the solvent was removed by evaporation, and to the residue was added 150 mL of methylene chloride and 50 mL of water. The aqueous layer was separated and reextracted with methylene chloride, then the organic extracts were combined and washed with brine, dried over MgSO4, and concentrated to leave an orange oily residue. The crude intermediate product was dissolved in 100 mL of refluxing toluene, to which was added 48 mg of p-toluenesulfonic acid, and the solution was heated at reflux for 30 min. The reaction was cooled to room temperature and 50 mL of water was added. The aqueous layer was extracted with ethyl acetate, and the organic extracts were combined, washed with brine, dried over MgSO4, and concentrated to leave an orange oil. This was dissolved in methylene chloride, which was washed with saturated sodium bicarbonate solution, water, dried and concentrated to afford 4.34 g of the title product (94% yield). NMR (CDCl3) δ:6.67 (s, 1H), 6.60 (s, 1H), 6.38 (d, 1H, J=10 Hz), 5.94(dt, 1H, J=4 Hz, J=10 Hz), 3.88 (s, 3H), 3.86 (s, 3H), 2.73 (t, 2H, J=8 Hz), 2.32-2.24 (m, 2H).

Aufarbeitung

  1. customMost of the solvent was removed by evaporation
  2. additionto the residue was added 150 mL of methylene chloride and 50 mL of water
  3. customThe aqueous layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto leave an orange oily residue
  8. temperaturethe solution was heated
  9. temperatureat reflux for 30 min
  10. temperatureThe reaction was cooled to room temperature
  11. extractionThe aqueous layer was extracted with ethyl acetate
  12. washwashed with brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated
  15. customto leave an orange oil
  16. washwhich was washed with saturated sodium bicarbonate solution, water
  17. customdried
  18. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0f47ddc9f1894a6f847fef1a749abf51
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597832

Notizen zur Reaktion

Wird geladen…