Methyl iodide → 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])=[N:14]1)[CH3:4].I[CH3:27]>C1COCC1>[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:27])=[N:14]1)[CH3:4]Participants
5
Procedure
Add sodium hydride (900 mg, 18 mmol, 60% suspension in mineral oil) to a suspension of 7-[3-(2-hydroxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (4.73 g, 15 mmol) and iodomethane (1.1 mL, 18 mmol) in THF (70 mL) at 0° C. under nitrogen and warm the mixture to room temperature to stir for 12 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (150 mL), wash with water (100 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9:1), to provide 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (3.75 g, 76%).
Workup
- customRemove the solvent under reduced pressure
- additiondilute the residue with ethyl acetate (150 mL)
- washwash with water (100 mL)
- dry with materialdry over sodium sulfate
- customRemove the solvent under reduced pressure
- custompurify the residue by flash column chromatography on silica gel
- washeluting with hexanes/ethyl acetate (9:1)
Sources & evidence
- ORD record
- ord-04771c1af57a4789b53e063626bfb235
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765796B2
Reaction notes
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