Benzyl Bromide → HCID 67255511, compound

HRID 2426974Notes

Reaction equation

HRID 2426974 reaction equation
[CH3:1][C:2]1([CH3:11])[O:6][C@:5]([CH3:10])([C:7]([O-:9])=[O:8])[CH2:4][O:3]1.[Li+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1([CH3:11])[O:6][C@:5]([CH3:10])([C:7]([O:9][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:8])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67256163HCID 67256163, compound

Product 1

HCID 67255511HCID 67255511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound prepared in Example 180 (5.9 g) in N,N-dimethylformamide (hereinafter abbreviated to DMF) (120 mL) were added benzyl bromide (4.3 mL) and potassium carbonate (9.9 g) and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered through Celite (trade name) and concentrated in vacuum condition to remove DMF. To the obtained residue was added water and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated in vacuum condition. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=6:1→4:1) to give the title compound (6.1 g) having the following physical data.

Workup

  1. filtrationThe reaction mixture was filtered through Celite (trade name)
  2. concentrationconcentrated in vacuum condition
  3. customto remove DMF
  4. additionTo the obtained residue was added water
  5. extractionthe organic layer was extracted with ethyl acetate
  6. dry with materialThe obtained organic layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuum condition
  8. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=6:1→4:1)

Sources & evidence

ORD record
ord-44022ea26b284a6f938f06979082f725
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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