Acetic Acid → Methyl 2-(4-(methylsulfonyl)phenyl)acetate

HRID 578909Notes

Reaction equation

HRID 578909 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Si](C=[N+]=[N-])(C)(C)[CH3:16].C(O)(=O)C>C(Cl)Cl.CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([O:14][CH3:16])=[O:13])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 5723454-Mesylphenylacetic acid

Product 1

HCID 16640928Methyl 2-(4-(methylsulfonyl)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Combined 2-(4-(methylsulfonyl)phenyl)acetic acid (1 g, 4.67 mmol) in DCM (15 mL) and MeOH (5 mL) and slowly added TMS-diazomethane (2 M in hexanes) (3.50 mL, 7.00 mmol) and the solution was stirred at 20° C. for 3 h. The reaction was quenched with acetic acid (0.134 mL, 2.334 mmol), let stir for 15 min, then concentrated in vacuo to give the title compound which was used without further purification. MS m/z 229 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59749488db2c4fdf879a719c292f26e4
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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