Methanol → HCID 58047066, compound

HRID 1888773Notes

Reaction equation

HRID 1888773 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:16][C:15]=3[CH:25]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(Cl)Cl.CO>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:16][C:15]=3[CH:25]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 22277759Boron tribromide dichloromethaneHCID 58047676HCID 58047676, compound

Product 1

HCID 58047066HCID 58047066, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(1-{5-[2-(4-methoxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)acetamide (922 mg, 2.73 mmol) obtained in Example 156 in methylene chloride (50 mL) was added 1M boron tribromide-methylene chloride solution (5.46 mL, 5.46 mmol) at −78° C., and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was warmed to 0° C., and methanol was added thereto. The solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from hexane-ethyl acetate to give the title compound (774 mg, yield 88%) as colorless crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate and water
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-3802ffb7cd76422795d3cf6ef8c952cb
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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