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Tetrahydrofuran → (E)-3-[3-ethoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-indan-1-yl-acrylamide

HRID 1446450
Notes
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Reaction equation

HRID 1446450 reaction equation
C1COCC1.[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1)[CH:12]=O)[CH3:7].C(OP([CH2:31][C:32](=[O:43])[NH:33][CH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35]1)(=O)OCC)C.O.[OH-].[Li+]>C(OCC)(=O)C.O>[CH2:6]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:31]/[C:32]([NH:33][CH:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:36][CH2:35]2)=[O:43])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1)[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 730140413-ethoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602465(Indan-1-ylcarbamoylmethyl)phosphonic acid diethyl ester

Product 1

HCID 59170821(E)-3-[3-ethoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-indan-1-yl-acrylamideYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF (8 mL) solution of 3-ethoxy-4-(4-methyl-1H-imidazole-1-yl)benzaldehyde (60 mg), (indan-1-ylcarbamoylmethyl)phosphonic acid diethyl ester (81 mg) and lithium hydroxide monohydrate (22 mg) were added, and the reaction mixture was agitated at room temperature for 14 hours. Water and ethyl acetate were added to the reaction solution after the reaction ended, and the organic layer was separated. The obtained organic layer was washed with a saturated sodium chloride solution, and the solvent was evaporated under reduced pressure after dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 1:4), and 23 mg (23%) of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. customthe solvent was evaporated under reduced pressure
  4. dry with materialafter dried over anhydrous magnesium sulfate
  5. customThe obtained residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 1:4)

Sources & evidence

ORD record
ord-d752fa94a1d5471c99e7181d5d1ba513
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07667041B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes