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N,N-Dipropyl-2-[[tetrahydro-5-[(phenylmethoxy)methyl]-2-furanyl]methoxy]acetamide → N,N-Dipropyl-2-[[tetrahydro-5-(hydroxymethyl)-2-furanyl]methoxy]acetamide

HRID 1278017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1278017
[CH2:1]([N:4]([CH2:24][CH2:25][CH3:26])[C:5](=[O:23])[CH2:6][O:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15]CC2C=CC=CC=2)[O:10]1)[CH2:2][CH3:3]>C(O)(=O)C.[Pd].C(O)C>[CH2:24]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:23])[CH2:6][O:7][CH2:8][CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[O:10]1)[CH2:25][CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 12888743N,N-Dipropyl-2-[[tetrahydro-5-[(phenylmethoxy)methyl]-2-furanyl]methoxy]acetamide

Produkt 1

HCID 12888744N,N-Dipropyl-2-[[tetrahydro-5-(hydroxymethyl)-2-furanyl]methoxy]acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

To a solution of 10.9 g of N,N-dipropyl-2-[[tetrahydro-5-[(phenylmethoxy)methyl]-2-furanyl]methoxy]acetamide (0.03 mole) in 125 ml of glacial acetic acid is added 2.5 g of 10% palladium on carbon. The mixture is hydrogenated at 55 psi over a period of 18 hours (debenzylation reaction taking up 98% of the calculated theory). The mixture is removed and the Pd/C filtered through a pad of "celite" filter aid. The acetic acid is then removed in vacuo yielding a pale yellow oil. The resulting oil is dissolved in 100 ml of ethanol and evaporated. The oil is then redissolved in ethanol and again evaporated in vacuo. The oil is then taken up in 200 ml of chloroform and washed with 100 ml of saturated NaHCO3 solution, 150 ml of water and finally with 200 ml of saturated NaCl solution. The CHCl3 layer is separated, dried over anhydrous Na2SO4 and then the CHCl3 is removed in vacuo yielding 7.6 g of crude product whih is vacuum distilled and the fraction distilling at 180°-183° @ 0.4 mm is collected yielding 7.1 g (87%) of the above compound.

Aufarbeitung

  1. custom(debenzylation reaction
  2. customThe mixture is removed
  3. filtrationthe Pd/C filtered through a pad of "celite"
  4. filtrationfilter aid
  5. customThe acetic acid is then removed in vacuo
  6. customyielding a pale yellow oil
  7. customevaporated
  8. dissolutionThe oil is then redissolved in ethanol
  9. customagain evaporated in vacuo
  10. washwashed with 100 ml of saturated NaHCO3 solution, 150 ml of water and finally with 200 ml of saturated NaCl solution
  11. customThe CHCl3 layer is separated
  12. dry with materialdried over anhydrous Na2SO4
  13. customthe CHCl3 is removed in vacuo
  14. customyielding 7.6 g of crude product whih
  15. distillationdistilled
  16. distillationthe fraction distilling at 180°-183° @ 0.4 mm
  17. customis collected

Quellen und Nachweise

ORD-Eintrag
ord-5c117397db4946cda77eb6334f170f46
Quelldatensatz
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04279902

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