Dimethyl Sulfate → 3-(Adamantan-1-yloxymethyl)-1-cyclohexyl-5-methoxy-1H-pyrazole

HRID 967801Notes

Reaction equation

HRID 967801 reaction equation
[C:1]12([O:11][CH2:12][C:13]3[CH:14]=[C:15]([OH:24])[N:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[N:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].S(OC)(O[CH3:31])(=O)=O>C1COCC1.CN(C=O)C>[C:1]12([O:11][CH2:12][C:13]3[CH:14]=[C:15]([O:24][CH3:31])[N:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[N:17]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178516267HCID 178516267, compound

Product 1

HCID 222919843-(Adamantan-1-yloxymethyl)-1-cyclohexyl-5-methoxy-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

5-(Adamantan-1-yloxymethyl)-2-cyclohexyl-2H-pyrazol-3-ol (0.29 g, 0.88 mmol) and sodium hydride (50 mg, 1.25 mmol of a 40% suspension in mineral oil) were stirred in THF-DMF (1:1) (10 mL) at 0° C. for 0.5 h, then allowed to warm to room temperature. Dimethyl sulphate (0.1 mL, 1 mmol) was added and the mixture stirred overnight. After concentration in vacuo, the mixture was poured into water (10 mL) and extracted with EtOAc (20 mL). The organic layer was separated washed with water (2×10 mL) and dried (MgSO4). Filtration and evaporation of the solvent afforded a yellow oil, which was purified by chromatography with EtOAc-hexane (1:1) as eluant. (0.24 g, 81%).

Workup

  1. concentrationAfter concentration in vacuo
  2. additionthe mixture was poured into water (10 mL)
  3. extractionextracted with EtOAc (20 mL)
  4. customThe organic layer was separated
  5. washwashed with water (2×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation of the solvent
  8. customafforded a yellow oil, which
  9. customwas purified by chromatography with EtOAc-hexane (1:1) as eluant

Sources & evidence

ORD record
ord-833b2c4f580e484e878eb94191baf682
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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