Furfural → 1-(Furan-2-yl)pentan-1-ol

HRID 5558

Reaktionsgleichung

Reaktionsgleichung von HRID 5558
[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([Mg]Br)[CH2:9][CH2:10][CH3:11].[NH4+].[Cl-]>C1COCC1>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:1]([OH:7])[CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

5

Edukt 3

HCID 7362FurfuralHCID 25517Ammonium ChlorideHCID 178418682HCID 178418682, Verbindung

Produkt 1

HCID 2492851-(Furan-2-yl)pentan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Freshly distilled furfural (233.5 g, 2.43 mol) was dissolved in 200 mL freshly distilled THF and added dropwise to a solution of butylmagnesium bromide (2.0 M in THF, 1460 mL, 2.92 mol) at 0° C. under dry nitrogen. After the addition was complete, the mixture was allowed to warm to room temperature overnight. The reaction was recooled to 0° C. and carefully poured into 2 L of cold sat. NH4Cl. The layers were separated, and the aqueous phase was extracted with ether. The combined organic layers were washed with saturated NaCl, dried over MgSO4, evaporated, and vacuum distilled to give 325.6 g (87%): bp 72°-73° C. (0.6 mmHg); 1H NMR (300 MHz, CDCl3) d 7.38 (1H, dd J=1 Hz), 6.33 (1H, m), 6.22 (1H, dd, J=3 Hz), 4.67 (1H, t, J=6 Hz), 2.9 (3H, m), 1.35 (4H, m), 0.90 (3H, t, J=7 Hz); mass spectrum (FAB): 170 (M+NH4).

Aufarbeitung

  1. additionAfter the addition
  2. customwas recooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined organic layers were washed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. distillationvacuum distilled
  9. customto give 325.6 g (87%)

Quellen und Nachweise

ORD-Eintrag
ord-6c6d592bcf1a42debe7854b152d5967a
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244910

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