Triethylamine → 1-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

HRID 732055Notes

Reaction equation

HRID 732055 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](Cl)=[N:6][OH:7].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15].C(N(CC)CC)C>C1C=CC=CC=1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH:15]=[C:14]([CH:13]([OH:16])[CH3:12])[O:7][N:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 724759113-Chloro-benzohydroximoyl chloride

Product 1

HCID 670707661-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro-benzohydroximoyl chloride (e.g. Kim, Jae Nyoung; Ryu, Eung K; J. Org. Chem. (1992), 57(24), 6649-50) (2.84 g, 14.8 mmol) was suspended in benzene (50 ml) and cooled to 0° C. 3-Butyn-2-ol (2.10 g, 29.9 mmol) and triethylamine (1.89 ml, 26.7 mmol) were added. The mixture was heated to 60° C. for 1.5 houes, cooled and diluted with benzene and 1N aqueous hydrochloric acid. After stirring, the separated benzene layer was evaporated to dryness and the crude purified via flash chromatography over silica using heptane/ethyl acetate=5/1 giving after drying in vacuo the title compound (0.49 g, 15%). 1H NMR (CDCl3), δ (ppm): 1.64 (d, 3 H), 5.07 (dq, 1 H), 6.50 (s, 1 H), 7.40 (m, 2 H), 7.68 (m, 1 H), 7.79 (m, 1 H),

Workup

  1. temperatureThe mixture was heated to 60° C. for 1.5 houes
  2. temperaturecooled
  3. customthe separated benzene layer was evaporated to dryness
  4. customthe crude purified via flash chromatography over silica
  5. dry with materialafter drying in vacuo the title compound (0.49 g, 15%)

Sources & evidence

ORD record
ord-f6dc243d6b7b468d8f740a9b7c9f0fff
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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