Magnesium → [(Heptyloxy)methyl]benzene

HRID 381620Notes

Reaction equation

HRID 381620 reaction equation
[Mg].[Cu](C#N)C#N.F[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:18][CH:19]([C:23]2[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=2)C2OC2)C2OC2)=[CH:10][CH:9]=1.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH2:14]([O:18][CH2:19][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 5462224MagnesiumHCID 21226206Ethyl acetate hexaneHCID 57037655p-Fluorophenylglycidyl etherHCID 178418260HCID 178418260, compound

Product 1

HCID 285096[(Heptyloxy)methyl]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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-4-6enzyloxy-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-9deaf4b3fc684f65bdec4da652001c84
Source dataset
uspto-grants-2001_10
Patent number
US06306895B1

Reaction notes

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