4-Benzyloxy-N-methoxy-N-methylphenylacetamide → 1-(4-Benzyloxy-phenyl)-pentan-2-one

HRID 401886Notes

Reaction equation

HRID 401886 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](N(OC)C)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Mg]Br)[CH2:23][CH3:24]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:17])[CH2:22][CH2:23][CH3:24])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 112546484-Benzyloxy-N-methoxy-N-methylphenylacetamideHCID 178455851HCID 178455851, compound

Product 1

HCID 673733611-(4-Benzyloxy-phenyl)-pentan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-acetamide (10.51 mmol, 3.0 g) in anhydrous THF at 0° C. was added n-propyl magnesium bromide (2.0 M solution in THF, 20 mL) drop-wise over 30 min. After completion of addition, the reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was cooled to 0° C. and quenched by adding saturated aqueous NH4Cl drop-wise followed by addition of ethyl acetate. The organic layer was separated, dried, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography by eluting with 5% ethyl acetate in hexanes to provide 1-(4-benzyloxy-phenyl)-pentan-2-one.

Workup

  1. additionAfter completion of addition
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched
  4. additionby adding saturated aqueous NH4Cl
  5. additiondrop-wise followed by addition of ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash column chromatography
  11. washby eluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-23094ee2c0d34f899cfda5f1c6e362a5
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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