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Acetic Acid → 1-acetoxy-1-[(1-hydroxy)indan-5-yl]-2-[2-(N,N-dimethylamino)ethoxy]ethane

HRID 976541
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 976541
[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([O:22]C1CCCCO1)[CH2:17][CH2:16]2)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2].C(O)(=O)C.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.O>[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([OH:22])[CH2:17][CH2:16]2)[CH2:6][O:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])(=[O:3])[CH3:2]
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Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 538846171-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane

Produkt 1

HCID 541925971-acetoxy-1-[(1-hydroxy)indan-5-yl]-2-[2-(N,N-dimethylamino)ethoxy]ethaneAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1.8 g of 1-acetoxy-2-[2-(N,N-dimethylamino)ethoxy]-1-[1-(tetrahydropyran-2-yloxy)indan-5-yl]ethane was added to 30 ml of a 4:2:1 mixed solution of acetic acid, tetrahydrofuran and water. The resulting mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled and added to a mixture of 100 ml of water and 100 ml of diethyl ether. The resulting mixture was adjusted to pH 8.5 with potassium carbonate. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: chloroform/ethanol=10/1) to obtain 1.0 g of oily 1-acetoxy-1-[(1-hydroxy)indan-5-yl]-2-[2-(N,N-dimethylamino)ethoxy]ethane (compound No. 296).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (eluant: chloroform/ethanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-80cfd9c70dec45aeb635afc1ef0b1224
Quelldatensatz
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05612381

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