Ammonium Chloride → HCID 22985555, compound

HRID 986940Notes

Reaction equation

HRID 986940 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[C:15]([N:19]1[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([CH:27]=[O:28])=[N:20]1)([CH3:18])([CH3:17])[CH3:16].[Cl-].[NH4+].C(OCC)(=O)C.CCCCCC>O1CCCC1.[Li]CCCC>[C:15]([N:19]1[C:23]([CH:24]([CH3:25])[CH3:26])=[CH:22][C:21]([CH:27]([OH:28])[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=3)=[CH:4][CH:3]=2)=[N:20]1)([CH3:17])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 21226206Ethyl acetate hexaneHCID 22493532HCID 22493532, compound

Product 1

HCID 22985555HCID 22985555, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Procedure

To 20 ml of a solution of 1.15 g of 4-bromo-1-(4,4-dimethyl-1,3-oxazolin-2-yl)benzene in tetrahydrofuran, 3.23 ml of n-BuLi (1.53M hexane solution) were added dropwise at −78° C. under stirring, followed by stirring at the same temperature for 15 minutes. To the reaction mixture was added dropwise a solution of 0.8 g of 1-tert-butyl-5-isopropylpyrazole-3-carbaldehyde in 5 ml of tetrahydrofuran. The resulting mixture was stirred for 30 minutes. After the reaction, 10 ml of a saturated aqueous solution of ammonium chloride were added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 50% ethyl acetate/n-hexane), whereby 0.82 g of the title compound was obtained in the form of a colorless oil.

Workup

  1. stirringby stirring at the same temperature for 15 minutes
  2. stirringThe resulting mixture was stirred for 30 minutes
  3. additionwere added to the reaction mixture
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue so obtained

Sources & evidence

ORD record
ord-82201d483e0b43c38ff5978371b5bcf2
Source dataset
uspto-grants-2003_10
Patent number
US06630463B2

Reaction notes

Loading…