3,4-dihydro-2H-pyran → (E)-N-(3-methyl-4-(3-(3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acryloyl)-phenyl)acetamide

HRID 884664Notes

Reaction equation

HRID 884664 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[CH3:22])=[O:11])=[CH:4][C:3]=1[CH3:23].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1>C(Cl)Cl>[CH3:22][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][C:12]=1[C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]1[CH:6]=[CH:7][C:2]([O:1][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:24]2)=[C:3]([CH3:23])[CH:4]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 59349186(E)-N-(4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenyl)acetamide

Product 1

HCID 59349184(E)-N-(3-methyl-4-(3-(3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acryloyl)-phenyl)acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-N-(4-(3-(4-hydroxy-3-methylphenyl)acryloyl)-3-methylphenyl)acetamide (100 mg, 0.32 mmol) in DCM was added 300 mg of H2SO4/SiO2 (cat. amount), and 3,4-dihydro-2H-pyran (500 mg, 5.9 mmol). The reaction mixture was stirred for 1 h at room temperature. The resulting slurry was filtered, concentrated under reduced pressure, and the product was purified by column chromatography (EtOAc/Hex, 10% to 50% gradient), resulting in 80 mg (78%) of the title compound. MS (EI) for C24H27NO4: 394 (MH+).

Workup

  1. filtrationThe resulting slurry was filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe product was purified by column chromatography (EtOAc/Hex, 10% to 50% gradient)

Sources & evidence

ORD record
ord-76dd5eb427cc4fd38bdc463ba6917793
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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