Water → HCID 58047024, compound

HRID 1888774Notes

Reaction equation

HRID 1888774 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:15][C:14]=3[CH:24]=2)=[CH:4][CH:3]=1.Br[CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:26]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:15][C:14]=3[CH:24]=2)=[CH:4][CH:3]=1)[CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 58047066HCID 58047066, compound

Product 1

HCID 58047024HCID 58047024, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of N-(1-{5-[2-(4-hydroxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)acetamide (333 mg, 1.03 mmol) obtained in Example 157, bromopropane (1.08 g, 6.37 mmol) and potassium carbonate (924 mg, 6.68 mmol) in DMF (10 mL) was stirred at 80° C. for 2 days. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solution was applied to silica gel column chromatography (hexane:ethyl acetate=9:11 to 0:1), and recrystallized from hexane-ethyl acetate to give the title compound (294 mg, yield 78%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-2cbf5226c5ec47af989a9175afb8c04b
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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