Acetaldehyde → HCID 57625097, Verbindung

HRID 1363508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363508
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:16])[NH:12][CH2:13][CH2:14][N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:17](=O)[CH3:18].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:17]([N:15]1[CH2:14][CH2:13][NH:12][C:11](=[O:16])[CH:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:18]

Komponenten

7

Edukt 4

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 57625103HCID 57625103, Verbindung

Produkt 1

HCID 57625097HCID 57625097, VerbindungAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with 31 (2.78 g, 12.7 mmol), acetaldehyde (727 mg, 16.5 mmol) and anhydrous methanol (40 mL). A solution of sodium cyanoborohydride (2.4 g, 38 mmol) and anhydrous zinc chloride (2.6 g, 19.1 mmol) in anhydrous methanol (40 mL) was added, and the reaction was stirred at room temperature for 1 h. After this time, 1N aqueous sodium hydroxide (25 mL) was added, and the methanol was evaporated under reduced pressure. The remaining aqueous solution was extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with water (100 mL) and brine (100 mL) and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure to afford a 98% yield (3.20 g) of 32 as a yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 8.18 (d, 2H, J=8.5 Hz), 8.02 (d, 1H, J=4.0 Hz), 7.66 (d, 2H, J=8.5 Hz), 4.06 (s, 1H), 3.39 (td, 1H, J=12.0, 4.0 Hz), 3.22 (m, 1H), 3.07 (dt, 1H, J=12.0, 3.0 Hz), 2.50 (m, 1H), 2.37 (m, 1H), 2.21 (m, 1H), 0.91 (t, 3H, J=8.5 Hz); MS (ESI+) m/z 250 (M+H).

Aufarbeitung

  1. customA 10-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customthe methanol was evaporated under reduced pressure
  4. extractionThe remaining aqueous solution was extracted with ethyl acetate (3×100 mL)
  5. washwashed with water (100 mL) and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e8ca62c174147efb46b974ef8f2f1cc
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884108B2

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