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

HRID 584379Notes

Reaction equation

HRID 584379 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-f9fe991c0e7b4671babdaaf2fa46fa31
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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