Reaktion #5654

Reaktionsgleichung

furfural

butylmagnesium bromide

NH4Cl

→

Racemic 1-(2-furyl)-1-pentanol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Sonstigewas recooled to 0° C.
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous phase was extracted with ether
5. 5
   WaschenThe combined organic layers were washed with saturated NaCl
6. 6
   Trocknendried over MgSO4
7. 7
   Sonstigeevaporated
8. 8
   workup.DISTILLATIONvacuum distilled
9. 9
   Sonstigeto give 325.6 g (87%)

Vorschrift

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).

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