Tetrahydrofuran → HCID 11776502, compound

HRID 1180375Notes

Reaction equation

HRID 1180375 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:2].[C:13]1([Mg]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCCC1>ClCCl>[OH:2][CH:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 15294Methyl 4-FormylbenzoateHCID 178478979HCID 178478979, compound

Product 1

HCID 11776502HCID 11776502, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-formylbenzoate (2.83 g, 17.2 mmoles) at −78° C. in 60 mL of dichloromethane is added 10 mL a 2.0 M solution of phenylmagnesium chloride in tetrahydrofuran (20.0 mmoles) over 7 minutes. After stirring for an additional 20 minutes, the reaction was quenched with methanol then with saturated aqueous ammonium chloride. The aqueous layer was acidified with 1N hydrochloric acid and the phases were separated. The organic portion was washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. Removal of the volatiles under reduced pressure and purification over silica gel afforded the title ester.

Workup

  1. customthe reaction was quenched with methanol
  2. customthe phases were separated
  3. washThe organic portion was washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the volatiles
  6. customunder reduced pressure and purification over silica gel

Sources & evidence

ORD record
ord-475bbdda556b4f1ab34582f80123769a
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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