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Acetic Acid → Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate

HRID 1949992
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1949992
O.[PH2]([O-])=O.[Na+].[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#N)=[CH:18][CH:17]=1)([CH3:9])([CH3:8])[CH3:7].N1C=CC=CC=1.C(O)(=[O:35])C>O.[Ni]>[C:6]([O:10][C:11](=[O:26])[NH:12][C:13]([CH3:25])([CH3:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:35])=[CH:18][CH:17]=1)([CH3:9])([CH3:8])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 1049PyridineHCID 57934408tert-Butyl [2-(4-cyanophenoxy)-1,1-dimethylethyl]carbamateHCID 178418950HCID 178418950, Verbindung

Produkt 1

HCID 57934200Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935
Nickel
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

The title compound was synthesized by referring to J. Chem. Soc., 1962, 3961. To a solution of sodium hypophosphite monohydrate (1.5 g) in water (3 ml) were sequentially added tert-butyl[2-(4-cyanophenoxy)-1,1-dimethylethyl]carbamate (500 mg), pyridine (10 ml) and acetic acid (5 ml). While stirring at room temperature, Raney nickel (50% suspension in water) (2 ml) was added dropwise to the reaction mixture and the solution was stirred for 15 minutes at room temperature and for 1 hour at 40° C. After filtration through celite pad and several wash with tetrahydrofuran and methanol, the solvent was evaporated in vacuo, and the residue was neutralized by adding a saturated aqueous solution of sodium bicarbonate. After extraction with ethyl acetate, the solution was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (443 mg).

Aufarbeitung

  1. customThe title compound was synthesized
  2. stirringthe solution was stirred for 15 minutes at room temperature and for 1 hour at 40° C
  3. filtrationAfter filtration through celite pad
  4. washseveral wash with tetrahydrofuran and methanol
  5. customthe solvent was evaporated in vacuo
  6. additionby adding a saturated aqueous solution of sodium bicarbonate
  7. extractionAfter extraction with ethyl acetate
  8. washthe solution was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-aeec60278c3f409781aa82aaed5d498c
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399520B2

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