3-Oxabicyclo(3.2.0)heptane-2,4-dione → 2-(4-Methoxy-benzoyl)-cyclobutanecarboxylic acid

HRID 2042593Notes

Reaction equation

HRID 2042593 reaction equation
[CH:1]12[CH2:7][CH2:6][CH:5]1[C:4](=[O:8])[O:3][C:2]2=[O:9].C([Mg]Br)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:4]([CH:5]2[CH2:6][CH2:7][CH:1]2[C:2]([OH:3])=[O:9])=[O:8])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 1382613-Oxabicyclo(3.2.0)heptane-2,4-dioneHCID 178418276HCID 178418276, compound

Product 1

HCID 596519352-(4-Methoxy-benzoyl)-cyclobutanecarboxylic acidYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 3-oxabicyclo[3.2.0]heptane-2,4-dione (8.00 g, 63.4 mmol) in THF (90.00 mL) at −78° C. was added 0.500 M of p-anisyl magnesium bromide (133 mL, 66.6 mmol) in THF (90 mL) dropwise. After stirring at −78° C. for 2 h, the reaction was quenched with ice cold water and concentrated. The aqueous layer was acidified and the white solid was filtered off and dried to obtain 9.72 g product (65%); MS m/z 233 (M−H).

Workup

  1. customthe reaction was quenched with ice cold water
  2. concentrationconcentrated
  3. filtrationthe white solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-1188584b8f9844b1bf9f5c04d906c226
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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