Lithium Hydroxide → HCID 54596739, compound

HRID 2167304Notes

Reaction equation

HRID 2167304 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][C:3]=1[N:16]1[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[N:17]1.[Li+].[OH-]>CO>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:4][C:3]=1[N:16]1[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[N:17]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58506478HCID 58506478, compound

Product 1

HCID 54596739HCID 54596739, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)phenyl)-1H-pyrazole-3-carboxylate 4 (70 mg, 0.208 mmol, 1.00 equiv) in methanol (10 mL), LiOH (50%, 6 mg, 0.250 mmol, 1.20 equiv) was added. The resulting solution was stirred overnight at room temperature. The solvent was concentrated under vacuum, the residue was applied onto a silica gel column and eluted with DCM/MeOH (3/1). This resulted in 60 mg (89%) of 1-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)-phenyl)-1H-pyrazole-3-carboxylic acid 5 as a green oil. 1H NMR (300 MHz, CDCl3, n=2): δ 8.00-8.10 (m, 1H), 7.35-7.60 (m, 1H), 6.85-7.00 (m, 1H), 6.30-6.70 (m, 2H), 4.10-4.15 (m, 2H), 3.70-3.85 (m, 2H), 3.45-3.70 (m, 4H), 3.43 (s, 3H). LC-MS: m/z=323 (MH)

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. washeluted with DCM/MeOH (3/1)
  3. customThis resulted in 60 mg (89%) of 1-(2-hydroxy-4-(2-(2-methoxyethoxy)ethoxy)-phenyl)-1H-pyrazole-3-carboxylic acid 5 as a green oil

Sources & evidence

ORD record
ord-f3ba98ed37054e43a57b286b9392e227
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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