5-bromo-N,N-diethyl-2-furamide → 5-[3-[(6-Bromohexyl)oxy]-1-propynyl]-N,N-diethyl-2-furancarboxamide

HRID 1086899Notes

Reaction equation

HRID 1086899 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]#[CH:24]>>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:2]1[O:6][C:5]([C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 9323705-bromo-N,N-diethyl-2-furamideHCID 218955011-Bromo-6-(prop-2-YN-1-yloxy)hexane

Product 1

HCID 199961125-[3-[(6-Bromohexyl)oxy]-1-propynyl]-N,N-diethyl-2-furancarboxamideYield 95.4%

Procedure

5-Bromo-N,N-diethyl-2-furancarboxamide (2.0 g) was treated with 3-[(6-bromohexyl)oxy]-1-propyne (1.87 g) according to the method of Intermediate 9 except that the reaction mixture was stirred under nitrogen at 60° for 4h, and hexane-ether (5:1 then 2:1 then 1:1) was used as the eluant for FCC. This afforded the title compound as a dark yellow oil (2.98 g), t.l.c. (diethyl ether) Rf 0.35.

Sources & evidence

ORD record
ord-e69caf9f836e42adb4910b77506fef1b
Source dataset
uspto-grants-1991_07
Patent number
US05032609

Reaction notes

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