Pyrazole → 1-(4-(Benzyloxy)benzyl)-1H-pyrazole

HRID 1160330Notes

Reaction equation

HRID 1160330 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[K+].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:20][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 14797Potassium HydroxideHCID 700424-Benzyloxybenzyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 591327651-(4-(Benzyloxy)benzyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

After a mixture of pyrazole (7.73 mmol) and potassium hydroxide (7.73 mmol) in DMF (35 mL) was stirred at room temperature for 30 min., a solution of 1-(benzyloxy)-4-(chloromethyl)benzene (6.44 mmol) in DMF (7 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight and the product obtained from a standard aqueous work up. Column chromatography (1:2 ethyl acetate/hexane) of the residue yielded compound 58.1 as a white solid. LC-MS ESI (pos.) m/e: 265 (M+H); 1H NMR (500 MHz) (DMSO-d6) δ 7.79 (1H, m); 7.46 (3H, m); 7.40 (2H, m); 7.36 (1H, m); 7.21 (2H, d, J=9 Hz)); 5.27 (2H, s); 5.11 (2H, m).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customthe product obtained from a standard aqueous work up

Sources & evidence

ORD record
ord-4c896c0439314c379361be8c547b1df7
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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