((4-Bromobutoxy)methyl)benzene → [(Heptyloxy)methyl]benzene

HRID 413562Notes

Reaction equation

HRID 413562 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14](O)[CH2:15]OC1C=CC=CC=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].BrCCCCOCC1C=CC=CC=1.[Cu](C#N)C#N.FC1C=CC(C(OC(C2C=CC(F)=CC=2)C2OC2)C2OC2)=CC=1>C1COCC1.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 4422181((4-Bromobutoxy)methyl)benzeneHCID 5462224MagnesiumHCID 18533452(+/-)-7-Benzyloxy-1-(fluorophenoxy)-heptane-2-olHCID 57037655p-Fluorophenylglycidyl etherHCID 178418260HCID 178418260, compound

Product 1

HCID 285096[(Heptyloxy)methyl]benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Part 1: (±)-7-Benzyloxy-1-(fluorophenoxy)-heptane-2-ol (Scheme VIII; 42) Magnesium (2.4 g, 98 mmol) was added to a 250 ml flask and flame dried. Dry THF, 25 ml, and 1 ml of dibromoethane were then added. 1-Bromo-4-benzyloxy-butane 41 (12 g, 49.4 mmol) dissolved in 50 ml of dry THF was added dropwise and the reaction mixture was stirred at room temperature. After 1 hour, the reaction mixture is cooled in an ice-water bath and 90 mg of copper cyanide is added. After 10 minutes in an ice-bath, 4-fluorophenyl-glycidyl ether (5 g, 29.6 mmol) dissolved in 30 ml of dry THF is added slowly. The reaction is monitored by TLC (ethyl acetate:hexane 3:7). After 15 minutes, the reaction is quenched with saturated aqueous ammonium chloride, concentrated and partitioned between water-ethyl acetate. The ethyl acetate layer is then washed with brine, dried over Na2SO4 and concentrated to give the desired benzyloxy-heptane 42. The structure was confirmed by 1H-NMR.

Workup

  1. temperatureflame
  2. customdried
  3. additionDry THF, 25 ml, and 1 ml of dibromoethane were then added
  4. additionwas added dropwise
  5. temperaturethe reaction mixture is cooled in an ice-water bath
  6. waitAfter 10 minutes in an ice-bath
  7. additionis added slowly
  8. waitAfter 15 minutes
  9. customthe reaction is quenched with saturated aqueous ammonium chloride
  10. concentrationconcentrated
  11. custompartitioned between water-ethyl acetate
  12. washThe ethyl acetate layer is then washed with brine
  13. dry with materialdried over Na2SO4
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-dc59415b6bd14fc88aedef8855a703ed
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Reaction notes

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