Pyrrole → 2-[(E)-2-phenylethenyl]-4-[4-[3-(1-pyrrolyl)propyl]phenoxymethyl]oxazole

HRID 322359Notes

Reaction equation

HRID 322359 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.CS(O[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[N:23]=[C:24](/[CH:27]=[CH:28]/[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:25][CH:26]=2)=[CH:16][CH:15]=1)(=O)=O>>[C:29]1(/[CH:28]=[CH:27]/[C:24]2[O:25][CH:26]=[C:22]([CH2:21][O:20][C:17]3[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][CH2:11][N:1]4[CH:5]=[CH:4][CH:3]=[CH:2]4)=[CH:19][CH:18]=3)[N:23]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 8027PyrroleHCID 155216743-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate

Product 1

HCID 220098162-[(E)-2-phenylethenyl]-4-[4-[3-(1-pyrrolyl)propyl]phenoxymethyl]oxazoleYield 57%

Procedure

In substantially the same manner as in Working Example 8, pyrrole was allowed to react with 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methansulfonate to give 2-[(E)-2-phenylethenyl]-4-[4-[3-(1-pyrrolyl)propyl]phenoxymethyl]oxazole. The yield was 57%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 108-109° C.

Sources & evidence

ORD record
ord-f816d6e60fa04942a9cabb5874f67fb4
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

Loading…