Benzoic acid, 2-(2-methoxy-2-oxoethyl)- → HCID 12241432, compound

HRID 660802Notes

Reaction equation

HRID 660802 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])=[O:4].B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 177459Benzoic acid, 2-(2-methoxy-2-oxoethyl)-HCID 2723981Borane;tetrahydrofuran

Product 1

HCID 12241432HCID 12241432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methoxycarbonylmethylbenzoic acid (1.84 g, 9.48 mmol) (Tetrahedron Lett. 39, 8563 (1998)) in THF (20 mL) at 0° C. is added dropwise borane THF solution (10.4 mL, 10.4 mmol) and the mixture is stirred at 0° C. for 4 h. The mixture is quenched with MeOH and the solvent is evaporated. To the residue is added EtOAc and the mixture is washed with brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound as an oil.

Workup

  1. customThe mixture is quenched with MeOH
  2. customthe solvent is evaporated
  3. additionTo the residue is added EtOAc
  4. washthe mixture is washed with brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-9cde7cdfa9d54da7a74350613c23831f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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