4-Aminophenol → (E)-N-(4-hydroxyphenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamide

HRID 884055Notes

Reaction equation

HRID 884055 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:15](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:16][CH3:17])/[C:12](O)=[O:13])=[CH:7][CH:6]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[OH:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:12](=[O:13])/[C:11](/[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=2)=[C:15](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[CH2:16][CH3:17])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 57693045(E)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enoic acid

Product 1

HCID 68732343(E)-N-(4-hydroxyphenyl)-2-(4-(methoxymethoxy)phenyl)-3-phenylpent-2-enamideYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3 (60 mg, 0.192 mmol), 4-aminophenol (23.0 mg, 0.211 mmol), 4-Dimethylaminopyridine (1.2 mg, 0.00982 mmol) and N,N-Diisopropylethylamine (37.2 mg, 0.287 mmol) in CH2Cl2 (2 ml) was added O-Benzotriazoyl-N,N,N′,N′-tetramethyluronium Hexafluorophosphate (76.5 mg, 0.202 mmol) under ice cooling, and the mixture was stirred at 0° C. for 5 min, and at room temperature for 15 h. The reaction was quenched with saturated aqueous NaHCO3 under ice cooling, and the whole was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4, and then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 3:1 to 2:1) gave 6a (68%). 6a: colorless powder; 1H-NMR (CDCl3) δ 1.05 (3H, t, J=7.5 Hz), 2.77 (2H, t, J=7.5 Hz), 3.43 (3H, s), 5.09 (2H, s), 6.79 (4H, m), 7.00 (2H, d, J=8.8 Hz), 7.00 (1H, brs), 7.07 (2H, m), 7.15-7.22 (3H, m), 7.37 (2H, d, J=8.8 Hz).

Workup

  1. waitat room temperature for 15 h
  2. customThe reaction was quenched with saturated aqueous NaHCO3 under ice cooling
  3. extractionthe whole was extracted with CHCl3
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by silica gel flash column chromatography (eluent: hexane/AcOEt, 3:1 to 2:1)

Sources & evidence

ORD record
ord-897125f21db14a7caaf0602529f38c13
Source dataset
uspto-grants-2012_08
Patent number
US08236987B2

Reaction notes

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