Sodium Hydroxide → HCID 68537893, compound

HRID 1993681Notes

Reaction equation

HRID 1993681 reaction equation
C[O:2][C:3]([C:5]1[N:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[N:7]=[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)=[O:4].[OH-].[Na+]>CO>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([N:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:9][C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])=[N:7]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68535338Methyl 1-(4-methylphenyl)-3-(trimethylsilyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 68537893HCID 68537893, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Place 2-p-tolyl-5-trimethylsilanyl-2H-pyrazole-3-carboxylic acid methyl ester (665 mg, 2.30 mmol) in methanol (25 mL). Add 1 N NaOH (10 mL, 10 mmol) and heat to 50° C. for 4 hours. Cool to room temperature and concentrate under reduced pressure. Add saturated aq. sodium bicarbonate solution and CH2Cl2. Separate organic layer and extract aqueous layer with CH2Cl2 (2×25 mL). Combine organic extracts, dry over Mg2SO4, filter, and concentrate under reduced pressure to yield 620 mg (98%) of 2-p-tolyl-5-trimethylsilanyl-2H-pyrazole-3-carboxylic acid. MS(ES+): m/z=275.3 [M+H].

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate under reduced pressure
  3. extractionSeparate organic layer and extract aqueous layer with CH2Cl2 (2×25 mL)
  4. dry with materialCombine organic extracts, dry over Mg2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-144c48a6ee1c4f439a47fc8e8a8123a3
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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