4-(Chloromethyl)-2-(3,4-dihydronaphthalen-2-yl)oxazole → 2-(3,4-Dihydro-2-naphthyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

HRID 322374Notes

Reaction equation

HRID 322374 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:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[O:21][CH:22]=1>>[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][C:23]=1[C:20]1[O:21][CH:22]=[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 220096374-(Chloromethyl)-2-(3,4-dihydronaphthalen-2-yl)oxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 220096842-(3,4-Dihydro-2-naphthyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazoleYield 42%

Procedure

In substantially the same manner as in Working Example 37, 1-[3-(4-hydroxyphenyl)propyl]imidazole was allowed to react with 4-chloromethyl-2-(3,4-dihydro-2-naphthyl)oxazole to give 2-(3,4-dihydro-2-naphthyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole. The yield was 42%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 99-100° C.

Sources & evidence

ORD record
ord-a6f22cafd98b4a0a861aa6708593fbca
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

Loading…