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

HRID 2168588Notes

Reaction equation

HRID 2168588 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]Cl)[CH2:23][CH2:24][CH3:25]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:17])[CH2:22][CH2:23][CH2:24][CH3:25])=[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 178418265HCID 178418265, compound

Product 1

HCID 673734141-(4-Benzyloxy-phenyl)-hexan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-acetamide (42.1 mmol, 12.0 g) in anhydrous THF at −10° C. was added n-butyl magnesium chloride (2.0 M solution in THF, 92.6 mmol, 46.3 mL) drop-wise. 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 with 1.0 N HCl by adding drop-wise. The reaction mixture was poured into water, extracted with ethyl acetate, and the combined extract was washed with water followed by brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by column chromatography using 10% ethyl acetate in hexanes to provide 1-(4-benzyloxy-phenyl)-hexan-2-one.

Workup

  1. additionAfter completion of addition
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with 1.0 N HCl
  4. additionby adding drop-wise
  5. additionThe reaction mixture was poured into water
  6. extractionextracted with ethyl acetate
  7. extractionthe combined extract
  8. washwas washed with water
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-92a04b9cbcc84fa9a39f178d86c7e57c
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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