Propargyl alcohol → (3-Phenyl-5-isoxazolyl)methanol

HRID 717211

Reaction equation

HRID 717211 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1[C:15](=[O:16])[CH2:14][CH2:13]C1=O.C(O)C#C.C(N(CC)CC)C>ClCCl>[C:2]1([C:1]2[CH:13]=[C:14]([CH2:15][OH:16])[O:9][N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide2×

Product 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanolYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.0 mmol of benzaldehyde oxime and 30 mL of dry dichloromethane were placed in a 250 mL single-necked round-bottom flask. 1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) was added under stirring. After NCS was completely dissolved by slightly heating, 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 mL solution of 10.1 g (10.0 mmol) of triethylamine in dichloromethane. After the addition was complete, the system was refluxed. After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield.

Workup

  1. temperatureby slightly heating
  2. additionAfter the addition
  3. temperaturethe system was refluxed
  4. washthe mother liquor was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customseparated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-5429e1783feb4fff95493802e03cf19a
Source dataset
uspto-grants-2015_11
Patent number
US09193718B2

Linked notes

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