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Acetaldehyde, 2,2-dimethoxy- → HCID 58504215, Verbindung

HRID 2407785
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2407785
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:29])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:20][CH:19]=2)[CH2:13][CH2:12]1.[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(OCC)(=O)C>[CH3:30][O:31][CH:32]([O:35][CH3:36])[CH2:33][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:29])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[N:20][CH:19]=2)[CH2:13][CH2:12]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydrideHCID 58504086HCID 58504086, Verbindung

Produkt 1

HCID 58504215HCID 58504215, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittel
HCID 962
Water
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound prepared in Example 309 (0.613 g) was suspended in 1,2-dichloroethane (30 mL). 2,2-Dimethoxyacetaldehyde solution in water (60% by weight) (2.28 mL) and beaded molecular sieves were added and the reaction mixture stirred at room temperature for 4 hours. Sodium triacetoxyborohydride (2.62 g) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 2% (9:1 methanol/concentrated ammonium hydroxide)/dichloromethane) to furnish the title compound (0.555 g) with the following physical properties.

Aufarbeitung

  1. additionwere added
  2. stirringthe reaction mixture stirred at room temperature overnight
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude material, which
  8. customwas purified by flash column chromatography (eluant: 2% (9:1 methanol/concentrated ammonium hydroxide)/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-10c6f6b9acbd450a90d1156e98a26b84
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809538B2

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