3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate → 2-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2H-1,2,3-triazole

HRID 322349Notes

Reaction equation

HRID 322349 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N: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:2]4[N:3]=[CH:4][CH:5]=[N:1]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 155216743-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonateHCID 178418936HCID 178418936, compound

Product 1

HCID 220098642-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2H-1,2,3-triazoleYield 35%

Procedure

In substantially the same manner as in Working Example 8, 1,2,3-triazole was allowed to react with 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate. The reaction mixture was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1, v/v), 2-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2H-1,2,3-triazole was obtained. The yield was 35%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 103-104° C.

Workup

  1. washFrom the fraction eluted with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-e29483aaccd246a898c95750a364554c
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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