Water → HCID 21105731, compound

HRID 1354479Notes

Reaction equation

HRID 1354479 reaction equation
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])#[CH:16].C(N(CC)CC)C.O>O1CCCC1>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([C:2]2[CH:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH:20]=[O:21])[O:14][N:13]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27716443-EthynylbenzaldehydeHCID 73013045HCID 73013045, compound

Product 1

HCID 21105731HCID 21105731, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 ml) of 1-[chloro(hydroxyimino)methyl]-4-trifluoromethylbenzene (0.849 g) and 3-ethynylbenzaldehyde (0.521 g) in tetrahydrofuran was added dropwise a solution (10 ml) of triethylamine (1.12 ml) in tetrahydrofuran at 0° C. This mixture was stirred overnight at room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio) and recrystallized from hexane-ethyl acetate to give 3-[3-(4-trifluoromethylphenyl)-5-isoxazolyl]benzaldehyde (0.660 g, yield 52%) as colorless needle crystals. melting point: 151–152° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-e662725d578e45e1a822aa67694b188d
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

Loading…