Benzyl Bromide → HCID 67279294, compound

HRID 1842256Notes

Reaction equation

HRID 1842256 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][CH2:5][CH:6]([OH:10])[CH2:7][CH:8]=[CH2:9].C(Br)C1[CH:19]=[CH:18][CH:17]=[CH:16]C=1.[H-].[Na+].[Cl-].[NH4+].CN1C[CH2:29][CH2:28][C:27]1=O>C(OCC)(=O)C.O>[CH3:12][O:11][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][CH:6]([C:7]1[CH:29]=[CH:28][CH:27]=[CH:9][CH:8]=1)[O:10][CH2:19][CH2:18][CH:17]=[CH2:16]

Participants

8

Reactant 5

HCID 7498Benzyl BromideHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57827343HCID 57827343, compound

Product 1

HCID 67279294HCID 67279294, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7,7-Dimethoxyhept-1-en-4-ol obtained in Preparation Example 59-(1) (5.47 g) was dissolved in 1-methyl-2-pyrrolidinone (35 mL). Benzyl bromide (3.12 mL, specific gravity: 1.44 g/cm3) was added and the mixture was sufficiently cooled in an ice bath under a nitrogen atmosphere. Sodium hydride (60%, 2.12 g) was added, followed by stirring for one hour and 30 minutes. Water and saturated ammonium chloride were slowly added and then ethyl acetate was added, followed by further stirring. The aqueous layer was separated and then 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, and the solid was removed by filtration. The filtrate was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the title compound (4.14 g).

Workup

  1. temperaturethe mixture was sufficiently cooled in an ice bath under a nitrogen atmosphere
  2. customThe aqueous layer was separated
  3. washthe organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. customthe solid was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-daf3cc4a0d054d1a8aedebe7f9df6834
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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