Methyl vinyl sulfone → 5-methyl-1-((1-(2-(methylsulfonyl)ethoxy)cyclooctyl)methyl)-1H-pyrazole

HRID 336614Notes

Reaction equation

HRID 336614 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]([CH2:9][C:10]2([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=[CH:6][CH:5]=1.[CH:19]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH2:20].[NH4+].[Cl-]>O1CCCC1>[CH3:3][C:4]1[N:8]([CH2:9][C:10]2([O:18][CH2:20][CH2:19][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[N:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866812711-((5-methyl-1H-pyrazol-1-yl)methyl)cyclooctanol

Product 1

HCID 894992895-methyl-1-((1-(2-(methylsulfonyl)ethoxy)cyclooctyl)methyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 200 mg) was added to a stirred solution of EXAMPLE 65A (667 mg) in tetrahydrofuran (10 mL) and the mixture was stirred at room temperature for 30 minutes before the addition of methyl vinyl sulfone (1.27 g). The mixture was stirred at room temperature for 3 hours. Aqueous NH4Cl was added to quench the reaction and the mixture was extracted with ethyl acetate (three times) and the combined organic layers were washed with water and brine, dried over Na2SO4, and filtered. The filtrate was concentrated to provide the crude product.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate (three times)
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e904e647eef54c9caa2f46a1381f3240
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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