(S)-methyl 4-hydroxy-4-(3-methoxyphenyl)butanoate → (S)-dihydro-5-(3-methoxyphenyl)furan-2(3H)-one

HRID 1972243Notes

Reaction equation

HRID 1972243 reaction equation
O[C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH2:3][CH2:4][C:5]([O:7]C)=[O:6]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C@H:2]2[O:7][C:5](=[O:6])[CH2:4][CH2:3]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 59486062(S)-methyl 4-hydroxy-4-(3-methoxyphenyl)butanoate

Product 1

HCID 57202694(S)-dihydro-5-(3-methoxyphenyl)furan-2(3H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The (S)-methyl 4-hydroxy-4-(3-methoxyphenyl)butanoate (985 mg) is dissolved in CH2Cl2 (10 mL), and the solution is cooled to 0° C. Trifluoroacetic acid (˜4 drops) is added and the mixture is stirred for 8 h at room temperature to complete the lactonization. The reaction is quenched with aqueous sodium bicarbonate, and the organic layer is washed with water, dried (Na2SO4), and concentrated to yield 827 mg (100%) of (S)-dihydro-5-(3-methoxyphenyl)furan-2(3H)-one as a colorless oil.

Workup

  1. customThe reaction is quenched with aqueous sodium bicarbonate
  2. washthe organic layer is washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa421e281aa48c982484b61e579c722
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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