Water → HCID 22733365, compound

HRID 2084402Notes

Reaction equation

HRID 2084402 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][OH:8].[H-].[Na+].I[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:37]=[CH:36][C:19]([O:20][CH2:21][C:22]2[N:23]=[C:24](/[CH:27]=[CH:28]/[C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=3)[O:25][CH:26]=2)=[CH:18][CH:17]=1.O>CN(C=O)C>[Br:35][C:32]1[CH:31]=[CH:30][C:29](/[CH:28]=[CH:27]/[C:24]2[O:25][CH:26]=[C:22]([CH2:21][O:20][C:19]3[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:1]4[CH:5]=[CH:4][N:3]=[C:2]4[CH2:6][CH2:7][OH:8])=[CH:37][CH:36]=3)[N:23]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 150160802-(1H-imidazol-2-yl)ethan-1-olHCID 22733354HCID 22733354, compound

Product 1

HCID 22733365HCID 22733365, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(1H-imidazol-2-yl)-ethanol (449 mg) in DMF (10 ml), 60% oily sodium hydride (176 mg) was added under ice cooling. After stirring at room temperature for 30 minutes, 4-[[4-(4-iodobutyl)phenoxy)methyl]-2-[(E)-2-(4-bromophenyl)ethenyl]-1,3-oxazole (2.15 g) was added under ice cooling. After stirring overnight at room temperature, water was added under ice cooling. The reaction mixture was extracted with a mixture of ethyl acetate-THF. The extract was dried over magnesium sulfate, after which it was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to yield the titled compound (2.09 g) as a light-yellow crystal.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. extractionThe reaction mixture was extracted with a mixture of ethyl acetate-THF
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationafter which it was concentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0e2faf05faa247478a5421a86add9918
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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