3-Methyl-2-phenylbutanoic acid

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 HA solution of 165.8 g (0.87 mol) of 2-phenyl-3-methylbutyric acid methyl ester, 52.0 q (1.30 mol) of sodium hydroxide, 1200 ml of methanol and 600 ml of water was heated to reflux for one hour. 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 beta-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.EXAMPLE 41 Preparation of 1-Isopropyl-1-phenyl acetic acid analogs1 1 Fuji, K.; Node, M.; Tanaka, F.; Hosoi, S. Tetrahedron Letters 1989, 30, 2825. A 1.0 mole solution of a substituted phenyl acetic acid and dried THF under argon was chilled to -78 C. The solution was treated with 1 equivalent of a LiN(TMS)2 (1 molar solution in THF). After 30 minutes, 1 equivalent of TMSCl (1 molar solution in THF) was added to the chilled solution followed by 2.2 equivalents of the LiN(TMS)2. After 20 minutes, 10 equivalents of HMPA was added, followed by 30 equivalents of iodopropane. The resulting mixture was stirred at -78 C. (1 h) and quenched by the addition of aqueous 5% HCl. The aqueous phase was extracted with EtOAc and the organic extract was washed twice with water and once with saturated aqueous NaC1, dried (Na2 SO4), and concentrated in vacuo. Chromatography (PCTLC, SiO2, 10-50% EtOAc-hexane) afforded the alkylated product 37, which was concentrated in vacuo.Suitable examples of the substituted phenyl-acetic acids of the formula (II) are exemplified as follows. alpha-Ethyl-phenylacetic acid alpha-iso-Propyl-phenylacetic acid 4-Methyl-alpha-ethyl-phenylacetic acid 4-Methyl-alpha-iso-propyl-phenylacetic acid 4-Methoxy-alpha-ethyl-phenylacetic acid ...

Molecular Weight:178.23
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:178.099379685
Monoisotopic Mass:178.099379685
Topological Polar Surface Area:37.3
Heavy Atom Count:13
Complexity:169
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes