Methyl methoxyacetate → 1-(3-(Benzyloxy)phenyl)-2-methoxyethanone

HRID 1662578Notes

Reaction equation

HRID 1662578 reaction equation
C[O:2][CH2:3][C:4]([O:6][CH3:7])=O.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC>[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([C:3](=[O:2])[CH2:4][O:6][CH3:7])[CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 80507Methyl methoxyacetateHCID 178419633HCID 178419633, compound

Product 1

HCID 197934711-(3-(Benzyloxy)phenyl)-2-methoxyethanoneYield 14%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl methoxyacetate (available from Aldrich) (0.48 mL, 4.8 mmol) in ether (20 mL) was added 3-benzyloxyphenylmagnesium bromide (1.0 M in THF) (available from Aldrich) (5.0 mL, 5.0 mmol) dropwise at −78° C. The mixture was warmed to room temperature overnight, quenched with 1 N HCl, and diluted with EtOAc. The organic layers were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 102.A (0.17 g, 14% yield) as a pale yellow oil.

Workup

  1. customquenched with 1 N HCl
  2. additiondiluted with EtOAc
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-b3ce67e9f9e74982b84379a51273dc7a
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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