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Tetrahydrofuran → (2E)-3-[4-(tert-Butyl)phenyl]-N-[3-(2-hydroxyethoxy)phenyl]prop-2-enamide

HRID 730260
Notes
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Reaction equation

HRID 730260 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C[O:26][CH2:25][CH2:24]1.BrCCO>[OH-].[Na+]>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:24][CH2:25][OH:26])[CH:17]=2)=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 108982-BromoethanolHCID 10214883(2E)-3-[4-(tert-Butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide

Product 1

HCID 10193484(2E)-3-[4-(tert-Butyl)phenyl]-N-[3-(2-hydroxyethoxy)phenyl]prop-2-enamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

To a round-bottomed flask, equipped with magnetic stirring and reflux condenser, was added (2E)-3-[4-(tert-butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide, Example 23, (200 mg, 0.68 mmol), THF (10 mL), 2-bromoethanol (200 uL, 2.80 mmol, Aldrich) and 5 N NaOH (10 mL). The reaction mixture was stirred at reflux for 5 h. After allowing to cool to 25° C., the mixture was extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (2:1 hexane:EtOAc) provided the title product as a colorless oil. MS (ESI, pos. ion) m/z: 340 (M+1).

Workup

  1. customTo a round-bottomed flask, equipped
  2. temperaturereflux condenser
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 5 h
  5. extractionthe mixture was extracted with EtOAc (20 mL)
  6. extractionThe organic extract
  7. washwas washed with water (20 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by silica gel chromatography (2:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-d573b4fff0824ce0958097b755df3969
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582657B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes