Propanal → HCID 178459257, Verbindung

HRID 1968946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968946
[CH:1](=[O:4])[CH2:2][CH3:3].CC([Si](C)(C)O[C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)(C)C.[Bi](Br)(Br)Br.C([SiH](CC)CC)C>C(#N)C>[CH2:1]([O:4][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1)[CH2:2][CH3:3]

Komponenten

6

Edukt 4

HCID 527PropanalHCID 12052TriethylsilaneHCID 82232bismuth(III) bromideHCID 178472501HCID 178472501, Verbindung

Produkt 1

HCID 178459257HCID 178459257, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Propionaldehyde (6.4 g) in acetonitrile (50 mL) was added over 30 minutes to a solution of cis/trans ethyl 4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}cyclohexanecarboxylate (D1, 25.2 g), bismuth tribromide (4.4 g) and triethylsilane (17.5 mL) in acetonitrile (300 mL) and the mixture was stirred for a further 1.5 hours. The solvent was partially removed then the residue was treated with ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried with anhydrous sodium sulphate and the solvent was removed to give the title compounds contaminated with silicone residues (39.1 g).

Aufarbeitung

  1. customThe solvent was partially removed
  2. additionthe residue was treated with ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulphate
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-233e234679114ce8863c8491940f4efb
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426443B2

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