Sodium hydride → 7-[3-(2-Hydroxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester

HRID 1039178Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[N:4]1.[CH2:15]([O:17][C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)[CH3:16]>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[N:4]1)[CH3:16]

Participants

Conditions

Temperature: 75 °C

Procedure

Add sodium hydride (1.50 g, 31 mmol, 60% suspension in mineral oil) to a suspension of 2-(1H-pyrazol-3-yl)phenol (5.0 g, 31 mmol) and 7-bromoheptanoic acid ethyl ester (7.4 g, 31 mmol) in DMF (75 mL) at room temperature under nitrogen and heat the mixture at 75° C. for 16 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (300 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-hydroxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (4.73 g, 48%).

Workup

customRemove the solvent under reduced pressure
additiondilute the residue with ethyl acetate (300 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-b68a271f4adb459f901f8362c6e03cf8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552039B2

Reaction notes

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