Acetic Acid → HCID 67513543, compound

HRID 1508461Notes

Reaction equation

HRID 1508461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:17].C(O)(=O)C>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([O:13][CH3:17])=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 3168043-(4-methoxyphenyl)-3-methylbutanoic acid

Product 1

HCID 67513543HCID 67513543, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

3-(4-methoxyphenyl)-3-methylbutanoic acid (513 mg, 2.463 mmol) was dissolved in toluene (13.3 ml) and methanol (2 ml). TMS-diazomethane (1.848 ml, 3.70 mmol) was added dropwise. Evolution of gas was observed, and a yellow color persisted. After 45 minutes, the reaction was quenched with acetic acid (200 uL, 3.5 mmol). The reaction was concentrated, and the residue was purified by flash chromatography on silica gel with 0 to 75% EtOAc/hexanes to afford methyl 3-(4-methoxyphenyl)-3-methylbutanoate. 1H NMR (CDCl3, 500 MHz) δ 7.28 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 3.79 (s, 3H), 3.54 (s, 3H), 2.59 (s, 2H), 1.43 (s, 6H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica gel with 0 to 75% EtOAc/hexanes

Sources & evidence

ORD record
ord-a5877b0af0ba4b5aa410c29177a889c0
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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