1-Iodopentane → 1-((tert-Butyldiphenylsilyloxy)methyl)-2-chloro-4-(n-pentyl)benzene

HRID 1072885Notes

Reaction equation

HRID 1072885 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Si:7]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Mg]Br)=[CH:28][C:27]=1[Cl:34])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)P(=O)(N(C)C)N(C)C.O1CCCC1>[Si:7]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:28][C:27]=1[Cl:34])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 123351-IodopentaneHCID 178455507HCID 178455507, compound

Product 1

HCID 223883821-((tert-Butyldiphenylsilyloxy)methyl)-2-chloro-4-(n-pentyl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
60 °C

Procedure

Then, 1-iodopentane (910 mg) was added to a suspension of copper bromide-dimethyl sulfide complex (62 mg) in hexamethylphosphoric triamide (0.3 ml) under a nitrogen atmosphere, and the mixture was heated to 60° C. Thereto was dropwise added the above-mentioned solution (5 ml) of 4-((tert-butyldiphenylsilyloxy)methyl)-3-chlorophenyl magnesium bromide in tetrahydrofuran over 10 min after removal of unreacted magnesium. After completion of the dropwise addition, the reaction mixture was refluxed under heating for 2 hr. Aqueous ammonium chloride was added to the reaction mixture and the resulting product was extracted three times with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography (hexane) to give the objective compound (914 mg) as a colorless oil.

Workup

  1. customafter removal of unreacted magnesium
  2. additionAfter completion of the dropwise addition
  3. temperaturethe reaction mixture was refluxed
  4. temperatureunder heating for 2 hr
  5. additionAqueous ammonium chloride was added to the reaction mixture
  6. extractionthe resulting product was extracted three times with hexane
  7. washwashed successively with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7946903ba2a14feda18994d63be3cef6
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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