Formaldehyde → HCID 10401484, Verbindung

HRID 2245782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245782
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=1.[CH2:18]=O.[C:20]([BH3-])#[N:21].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:21]([CH3:20])[CH3:18])=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11777044Hexanoic acid, 6-[(4-aminophenyl)thio]-, methyl ester

Produkt 1

HCID 10401484HCID 10401484, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 6-(4-amino-phenylsulfanyl)-hexanoic acid methyl ester (2.5 g, 10 mmol) in methanol (20 mL) was added at 0° C. a 37% aqueous solution of formaldehyde (2.4 mL, 30 mmol) and a solution of sodium cyanoborohydride (2.5 g, 40 mmol) and zinc chloride (2.7 g, 20 mmol) in methanol (150 mL). The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was taken up in ethyl acetate (250 mL) and aqueous sodium hydroxide (100 mL, 2M). The organic layer was washed consecutively with aqueous sodium hydroxide (100 mL, 2M), distilled water (2×100 mL) and brine (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by flash chromatography (10:90:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give the title compound (2.2 g, 79%) as a colourless oil.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. washThe organic layer was washed consecutively with aqueous sodium hydroxide (100 mL, 2M)
  3. distillationdistilled water (2×100 mL) and brine (2×100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil that
  8. customwas purified by flash chromatography (10:90:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-495d6e46c5384ed2a0e490168090c0fa
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683185B2

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