Sodium Hydroxide → phenyl tetrahydrofuran-2-carboxylate

HRID 2229478Notes

Reaction equation

HRID 2229478 reaction equation
[C:1]1([C:7]2([C:12]([O:14]CC)=[O:13])[CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9][O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18467896HCID 18467896, compound

Product 1

HCID 18467999phenyl tetrahydrofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-phenyl-2-tetrahydrofuroate (170 mg, 0.77 mmol) in methanol (6 ml) was added 0.5N NaOH (1.5 ml, 0.75 mmol). After stirring at room temperature overnight, it was partitioned between dilute acetic acid and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with brine and dried over MgSO4, filtered and concentrated to afford the title compound as a white crystalline solid which was used without further purification. 400 MHz 1H NMR (CD3OD): δ 7.54 (m, 2H); 7.34 (m, 3H); 4.07 (m, 2H); 2.79 (m, 1H); 2.18 (m, 1H); 1.98 (m, 2H).

Workup

  1. customit was partitioned between dilute acetic acid and ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cee9833514b44bb88fcf3bee70dd72cf
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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