Ethyl bromoacetate → HCID 86597791, compound

HRID 749206Notes

Reaction equation

HRID 749206 reaction equation
[CH2:1]([C:4]1[C:12]2[O:11][N:10]=[C:9]([CH2:13][CH2:14][C:15]3[N:16]=[C:17]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=4[Cl:30])[O:18][C:19]=3[CH:20]([CH3:22])[CH3:21])[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:31])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CC(C)=O>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][O:31][C:5]1[CH:6]=[CH:7][C:8]2[C:9]([CH2:13][CH2:14][C:15]3[N:16]=[C:17]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=4[Cl:30])[O:18][C:19]=3[CH:20]([CH3:22])[CH3:21])=[N:10][O:11][C:12]=2[C:4]=1[CH2:1][CH:2]=[CH2:3])[CH3:44]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 135761795HCID 135761795, compound

Product 1

HCID 86597791HCID 86597791, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

The obtained 7-allyl-6-hydroxy-3-[2-[2-(2,4-dichlorophenyl)-5-isopropyl-4-oxazolyl]ethyl]-1,2-benzisoxazole (45 mg, 0.098 mmol) and potassium carbonate (20 mg, 0.147 mmol) was suspended in acetone (5.0 mL). An acetone solution of ethyl bromoacetate (25 mg, 0.147 mmol) was added to the suspension 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 (43 mg) as colorless oil (yield 80%).

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-3be4aec1b57b4ae1bd1f60415a03e1ae
Source dataset
uspto-grants-2008_07
Patent number
US07402597B2

Reaction notes

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