4-(4-Hydroxyphenyl)butanenitrile → 4-[4-[2-(Furan-2yl)-5-methyl-4-oxazolylmethoxy]phenyl]butyronitrile

HRID 233328Notes

Reaction equation

HRID 233328 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][C:24]#[N:25])=[CH:17][CH:16]=1>>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][C:24]#[N:25])=[CH:19][CH:20]=2)[N:4]=1

Participants

3

Reactant 2

HCID 137810254-(4-Hydroxyphenyl)butanenitrileHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 111100694-[4-[2-(Furan-2yl)-5-methyl-4-oxazolylmethoxy]phenyl]butyronitrile

Procedure

According to the method described for Reference Example 45, 4-chloromethyl-2-(furan-2-yl)-5-methyloxazole was allowed to react with 4-(4hydroxyphenyl)butyronitrile to give 4-[4-[2-(furan-2yl)-5-methyl-4-oxazolylmethoxy]phenyl]butyronitrile as an oily product. NMR(δ ppm in CDCl3): 1.85-2.05(2H,m), 2.31(2H,t,J=7Hz), 2.42(3H,s), 2.72(2H,t,J=7.5Hz), 4.97(2H,s), 6.52(1H,dd,J=3.5&2Hz), 6.9-7.0(3H,m), 7.10(2H,d,J=9Hz), 7.53(1H,dd,J=2&1Hz).

Sources & evidence

ORD record
ord-3cc472ce382b4921861f0cb4b2561b34
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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