Tetrahydrofuran → 1-(3-(Benzyloxy)phenyl)-2-methoxyethanone

HRID 1662500Notes

Reaction equation

HRID 1662500 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.C1COCC1>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

5

Reactant 3

HCID 8028TetrahydrofuranHCID 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 (20.0 mL) was added a 1.0 M solution of (3-(benzyloxy)phenyl)magnesium bromide 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 organics 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 1-(3-(benzyloxy)phenyl)-2-methoxyethanone (0.17 g, 14%) as a pale yellow oil.

Workup

  1. customquenched with 1 N HCl
  2. additiondiluted with EtOAc
  3. washThe organics 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-d963cb22a6b84a0f8aed88dd181cf27f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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