Water → Ethyl 3-(1,3-dimethyl-1H-indol-2-yl)-5-ethyl-4,5-dihydro-5-isoxazole-carboxylate

HRID 225952

Reaction equation

HRID 225952 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH:12]=[N:13][OH:14].[CH2:15]([C:17](=[CH2:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:16].Cl[O-].[Na+].O>ClCCl.C(N(CC)CC)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]1[CH2:23][C:17]([CH2:15][CH3:16])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][N:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 291416Ethyl 2-methylidenebutanoateHCID 23665760Sodium HypochloriteHCID 852718921,3-Dimethyl-1H-indol-2-aldehyde oxime

Product 1

HCID 68835063Ethyl 3-(1,3-dimethyl-1H-indol-2-yl)-5-ethyl-4,5-dihydro-5-isoxazole-carboxylateYield 35.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1,3-Dimethyl-1H-indol-2-aldehyde oxime derivative (356 mg, 2.07 mmol) was dissolved in dichloromethane (20 ml), and the mixture was kept at 0□. Ethyl 2-ethylacrylate (345 mg, 1.3 Eq) and triethylamine (6 drops) were dissolved in dichloromethane (5 ml), thus obtained solution was slowly added to the above, and sodium hypochlorite solution (5.5 ml) was further added. The reaction solution was warmed to room temperature and stirred for 4 hours. Water (20 ml) was added, and the mixture was extracted with dichloromethane (40 ml×2), washed with aqueous sodium chloride solution (20 ml), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (15% ethyl acetate-hexane) to give the title compound (230 mg, Yield 35%).

Workup

  1. additionwas further added
  2. extractionthe mixture was extracted with dichloromethane (40 ml×2)
  3. washwashed with aqueous sodium chloride solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-427150645de04ad59bb5ae8c4cc2ae4b
Source dataset
uspto-grants-2009_07
Patent number
US07557133B2

Linked notes

Loading…