Allyl bromide → HCID 21928216, compound

HRID 749205Notes

Reaction equation

HRID 749205 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]2[C:6]([CH2:9][CH2:10][C:11]3[N:12]=[C:13]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[O:14][C:15]=3[CH:16]([CH3:18])[CH3:17])=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[CH:36]=[CH2:37]>CC(C)=O>[CH2:37]([O:1][C:2]1[CH:28]=[CH:27][C:5]2[C:6]([CH2:9][CH2:10][C:11]3[N:12]=[C:13]([C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=4[Cl:26])[O:14][C:15]=3[CH:16]([CH3:18])[CH3:17])=[N:7][O:8][C:4]=2[CH:3]=1)[CH:36]=[CH2:35]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 135761794HCID 135761794, compound

Product 1

HCID 21928216HCID 21928216, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The obtained 6-hydroxy-3-[2-[2-(2,4-dichlorophenyl)-5-isopropyl-4-oxazolyl]ethyl]-1,2-benzisoxazole (500 mg, 1.20 mmol) and potassium carbonate (249 mg, 1.80 mmol) were suspended in acetone (30 mL). Allyl bromide (217 mg, 1.80 mmol) was dropwise added to the suspension for 1 minute while cooling with ice. The mixture was allowed to room temperature, and stirred for 20 hours. After insoluble was filtered off, the filter cake was washed with acetone. The filtrate and washings were combined, and concentrated. The residue was purified by column chromatography on silica gel with hexane/ethyl acetate (4/1) to give the desired compound (420 mg) as colorless oil (yield 77%).

Workup

  1. temperaturewhile cooling with ice
  2. customwas allowed to room temperature
  3. filtrationAfter insoluble was filtered off
  4. washthe filter cake was washed with acetone
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-73195ed876e94ea699354235e56b28b7
Source dataset
uspto-grants-2008_07
Patent number
US07402597B2

Reaction notes

Loading…