Methanol → Methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate

HRID 1519550Notes

Reaction equation

HRID 1519550 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].CO.[CH2:18](Cl)Cl.C[Si](C=[N+]=[N-])(C)C>CCOCC>[CH3:18][O:14][C:13](=[O:15])[CH2:12][C:3]1[CH:4]=[C:5]([O:10][CH3:11])[C:6]([C:8]#[N:9])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 67513894(2-Chloro-4-cyano-5-methoxyphenyl)acetic acid

Product 1

HCID 77231255Methyl (2-chloro-4-cyano-5-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2-Chloro-4-cyano-5-methoxyphenyl)acetic acid (545 mg, 2.4 mmol) was taken up in 1:1 MeOH:DCM (50 mL) and excess 2M trimethylsilyldiazomethane in ether was added until the yellow color persisted, the excess was quenched with acetic acid and the solution was concentrated in vacuo. Flash chromatography (10-50% ethyl acetate/hexanes) gave the title ester as a white solid. 1H-NMR (500 MHz, CDCl3) δ ppm 3.703 (s, 3H), 3.767 (s, 2H), 3.897 (s, 3H), 6.896 (s, 1H), 7.526 (s, 1H).

Workup

  1. customthe excess was quenched with acetic acid
  2. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-8fe9aabcd6f145068bf7e3238e8b84a8
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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