ChemicalBook CAS DataBase List 2-FURANONE,4,5-DIHYDRO-3-PHENYL-

2-FURANONE,4,5-DIHYDRO-3-PHENYL- synthesis

11synthesis methods

Product Name:2-FURANONE,4,5-DIHYDRO-3-PHENYL-
CAS Number:6836-98-2
Molecular formula:C10H10O2
Molecular Weight:162.19

75-21-8
233 suppliers
$39.10/1mL

103-82-2
2 suppliers
$22.60/100g

6836-98-2
11 suppliers
$503.99/5MG

Yield:6836-98-2 58%

Reaction Conditions:

Stage #1: phenylacetic acidwith 1,2-diphenyl-1,2-disodiumethane in tetrahydrofuran at 0; for 2 h;Inert atmosphere;
Stage #2: oxirane in tetrahydrofuran at -30; for 0.5 h;Inert atmosphere;
Stage #3: with hydrogenchloride in water;regioselective reaction;

Steps:

4.4. Metalation of arylacetic acids 2, and reaction with electrophiles. General procedure

General procedure: To 5 mL of a 0.24 M solution of diorganometal 1b or 1c (1.2 mmol), chilled at 0 °C, was added a solution of the appropriate arylacetic acid 2 (1.1 mmol) dissolved in 5 mL of dry THF, and the resulting mixture was vigorously stirred for 2 h at 0 °C. To the resulting dark brown mixture, chilled at the same temperature, were added 1.7 mmol of the appropriate electrophile. The resulting mixture was vigorously stirred and allowed to reach rt overnight, after which time it was quenched by slow dropwise addition of H₂O (15 mL). The organic solvent was evaporated in vacuo and the resulting mixture was extracted with CH₂Cl₂ (3×10 mL). The aqueous phase was acidified with 1 N HCl, extracted with CH₂Cl₂ (3×10 mL), and the organic phases were collected, washed with H₂O (1×10 mL), brine (10 mL), dried (Na₂SO₄), and the solvent was evaporated. Crude reaction products were purified and characterized as reported below. The reaction mixture containing crude β-hydroxyacid 2df was quenched by adding it to 15 mL of 10% HCl containing about 15 g of crushed ice,¹⁴ and worked up as described above. After evaporation of the solvent, the resulting crude material was purified and characterized as reported below. Quenching with D₂O was realized as described in the above paragraph.