Ammonium Chloride → HCID 68438168, compound

HRID 1592822Notes

Reaction equation

HRID 1592822 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C([Li])(C)(C)C.C([O:23][C:24]1[C:28]([CH:29]=O)=[C:27]([CH3:31])[N:26]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:25]=1)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1.CO.[C].[Pd]>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([CH2:29][C:28]2[C:24](=[O:23])[NH:25][N:26]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:27]=2[CH3:31])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 728512-(4-Bromophenyl)ethanolHCID 17863259HCID 17863259, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 68438168HCID 68438168, compoundYield 30.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromophenethyl alcohol (0.21 g) in tetrahydrofuran (20 mL) was added tert-butyllithium (1.6 mol/L pentane solution, 1.5 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of 3-benzyloxy-4-formyl-5-methyl-1-phenyl-1H-pyrazole (0.10 g) in tetrahydrofuran (3 mL), and the mixture was warmed to 0° C. and stirred for 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2) to give an oily substance. The obtained oily substance was dissolved in methanol (4 mL). To the solution was added 10% palladium-carbon powder (0.044 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 17 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. Diethyl ether was added to the residue, and the resulting precipitates were collected by filtration and dried under reduced pressure to give the title compound (0.032 g).

Workup

  1. stirringstirred for 30 minutes
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2)
  7. customto give an oily substance
  8. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 17 hours
  9. customInsoluble materials were removed by filtration
  10. customthe solvent of the filtrate was removed under reduced pressure
  11. additionDiethyl ether was added to the residue
  12. customthe resulting precipitates
  13. filtrationwere collected by filtration
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-22f6564e2e9a4a289264301a76ebcc9e
Source dataset
uspto-grants-2007_11
Patent number
US07294618B2

Reaction notes

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