Ethyl Acetate → HCID 15790297, compound

HRID 2211095Notes

Reaction equation

HRID 2211095 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][OH:12])=[CH:6][CH:5]=1.Cl[C:24]1[N:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C(OCC)(=O)C>CCOCC>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:11][O:12][C:24]2[N:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 157666652-(4-Chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol

Product 1

HCID 15790297HCID 15790297, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a flask was charged 0.15 g (0.0034 mole) of 60% sodium hydride, washed with 2×30 mL hexane, in 20 mL of tetrahydrofuran. While stirring at room temperature, 1.0 g (0.0034 mole) of 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexan-1-ol was added. The slurry was stirred at room temperature and 0.39 g of 2-chloropyrimidine (0.0034 mole) was added. The reaction was stirred overnight after which TLC using ethyl acetate indicated the reaction was complete. The product was isolated from ether after quenching and washing with water. After drying and removal of the solvent, 1.30 g (100% yield) of an oil resulted.

Workup

  1. washwashed with 2×30 mL hexane, in 20 mL of tetrahydrofuran
  2. stirringThe slurry was stirred at room temperature
  3. stirringThe reaction was stirred overnight after which TLC
  4. customafter quenching
  5. washwashing with water
  6. customAfter drying

Sources & evidence

ORD record
ord-2e8cf97524ad4b0694e5dd2129cfa954
Source dataset
uspto-grants-1995_10
Patent number
US05462931

Reaction notes

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