Benzyl Bromide → HCID 57827270, compound

HRID 1693216Notes

Reaction equation

HRID 1693216 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][CH:12]([O:20][CH2:21][CH3:22])[CH2:13][CH:14]([OH:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[CH3:10].[H-].[Na+].[Cl-].[NH4+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CN(C=O)C>[CH2:21]([O:20][CH:12]([O:11][CH2:9][CH3:10])[CH2:13][CH:14]([O:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:15][CH2:16][CH:17]=[CH2:18])[CH3:22]

Participants

8

Reactant 4

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 57827354HCID 57827354, compound

Product 1

HCID 57827270HCID 57827270, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DMF (40 mL) and benzyl bromide (2.4 mL, specific gravity: 1.44 g/cm3) were added to 1,1-diethoxyhept-6-en-3-ol obtained in Preparation Example 57-(1) (3.71 g), and the mixture was cooled in an ice bath under a nitrogen atmosphere. Then, sodium hydride (60%, 883 mg) was added, followed by stirring for 60 minutes. Benzyl bromide (1.09 mL) was further added, followed by stirring for one hour. Sodium hydride (60%, 116 mg) was further added, and the mixture was stirred for one hour and 50 minutes while gradually warming to room temperature. Tetrabutylammonium iodide (680 mg) was further added, followed by stirring for one hour and 10 minutes. Water and a saturated ammonium chloride solution were slowly added. After stirring for a while, the aqueous layer was separated. The organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine. The resulting organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (4.06 g).

Workup

  1. temperaturethe mixture was cooled in an ice bath under a nitrogen atmosphere
  2. stirringby stirring for one hour
  3. stirringthe mixture was stirred for one hour and 50 minutes
  4. stirringby stirring for one hour and 10 minutes
  5. stirringAfter stirring for a while
  6. customthe aqueous layer was separated
  7. washThe organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine
  8. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9fd1d2dbbc3849b18b7d3be70b11912d
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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