Water → HCID 22932164, compound

HRID 1351090Notes

Reaction equation

HRID 1351090 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[N:11]([CH2:17][CH2:18][OH:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>ClCCl>[C:27]([O:19][CH2:18][CH2:17][N:11]1[C:12]([CH:14]([CH3:16])[CH3:15])=[CH:13][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:10]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22932162HCID 22932162, compound

Product 1

HCID 22932164HCID 22932164, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyloxy-1-(2-hydroxyethyl)-5-isopropyl-1H-pyrazole (2.41 g) in dichloromethane (45 mL) were added triethylamine (1.40 g) and benzoyl chloride (1.43 g) at 0° C., and the mixture was stirred for 30 minutes. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/6-1/1) to give the title compound (1.35 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/6-1/1)

Sources & evidence

ORD record
ord-a38bcd581d514dc986cd5157ea33c361
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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