Methyl iodide → 2-(2-Chloro-5-methoxy-phenyl)-propionic acid methyl ester

HRID 333805Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Cl:13].[CH:15]([N-]C(C)C)(C)C.[Li+].IC>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH:4]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Cl:13])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

2-Chloro-5-methoxy-benzeneacetic acid methyl ester (994 mg) was dissolved in THF and cooled to −78° C. Lithiumdiisopropylamide (2M in THF, 3.72 mL) was added drop wise and stirring was continued for 30 minutes. Iodomethane (879 mg, 0.39 mL) was added and stirring was continued for 30 minutes. The cooling bath was removed and the reaction was allowed to warm for 45 minutes. The mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate:heptane 1:3) to give the desired compound as a yellow oil (859 mg). 1H-NMR, (CDCl3): 7.27 (d, 1H), 6.85 (d, 1H), 6.74 (dd, 1H), 4.17 (q, 1H), 3.78 (s, 3H), 3.69 (s, 3H), 1.48 (d, 3H).

Workup

stirringstirring
waitwas continued for 30 minutes
customThe cooling bath was removed
temperatureto warm for 45 minutes
additionThe mixture was poured into water
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with brine
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by flash chromatography (silica gel, ethyl acetate:heptane 1:3)

Sources & evidence

ORD record: ord-44602da54d0747fd9cbb3e0b0a1610c3
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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