Benzyl Bromide → 1H-Pyrazole, 1-(phenylmethoxy)-

HRID 906576Notes

Reaction equation

HRID 906576 reaction equation
[N:1]1([OH:6])[CH:5]=[CH:4][CH:3]=[N:2]1.CCN(C(C)C)C(C)C.[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][CH:17]=1>C(Cl)Cl>[CH2:22]([O:6][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 30167331-hydroxy-1H-pyrazole

Product 1

HCID 100580151H-Pyrazole, 1-(phenylmethoxy)-Yield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of pyrazol-1-ol (1 g, 11.9 mmol) and i-Pr2NEt (2.02 mL, 11.9 mL) in DCM (15 mL) at 0° C. was added BnBr (4.09 mL, 23.8 mmol). The mixture was allowed to warm up to r.t. and stirred at this temperature for 22 h. The mixture was concentrated in vacuo to afford a yellow paste. The crude product was purified by flash chromatography (silica gel, hexanes/DCM/Et2O (100:0:0 to 80:10:10), Rf 0.23 in hexanes/DCM/Et2O (34:3:3)) to provide the title product as a yellow oil (1.17 g, 56%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford a yellow paste
  3. customThe crude product was purified by flash chromatography (silica gel, hexanes/DCM/Et2O (100:0:0 to 80:10:10), Rf 0.23 in hexanes/DCM/Et2O (34:3:3))

Sources & evidence

ORD record
ord-e84b6c22998449a29c228b53e9a719ce
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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