Water → (3-Phenyl-5-isoxazolyl)methanol

HRID 2299737Notes

Reaction equation

HRID 2299737 reaction equation
C(N(CC)CC)C.Cl[C:9](=[N:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:18]([OH:21])[C:19]#[CH:20].O>O1CCCC1>[C:10]1([C:9]2[CH:20]=[C:19]([CH2:18][OH:21])[O:17][N:16]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanolYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (7.28 ml) was added to a solution of α-chlorobenzaldehyde oxime (4.04 g) and 2-propyn-1-ol (1.66 ml) in tetrahydrofuran (130 ml) and stirred at room temperature for 4 days. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain (3-phenyl-5-isoxazolyl)methanol (3.42 g, yield 75%) as colorless crystals. m.p. 48-49° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a6684722b48d4976818ddb6132216b19
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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