1-[3-(4-Hydroxyphenyl)propyl]imidazole → 2-(2-Furyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazole

HRID 322423Notes

Reaction equation

HRID 322423 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH:3]=1.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)[O:21][C:22]=1[CH3:23]>>[O:25]1[CH:26]=[CH:27][CH:28]=[C:24]1[C:20]1[O:21][C:22]([CH3:23])=[C:18]([CH2:17][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)=[CH:4][CH:3]=2)[N:19]=1

Participants

3

Reactant 2

HCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazoleHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 220097792-(2-Furyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazoleYield 79%

Procedure

In substantially the same manner as in Working Example 72, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 4-chloromethyl-2-(2-furyl)-5-methyloxazole to give 2-(2-furyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-5-methyloxazole. The yield was 79%. Recrystallization from acetone-isopropyl ether gave colorless prisms, mp 89-90° C.

Sources & evidence

ORD record
ord-c52e4c649d8e4bd8840328382db407a6
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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