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

HRID 57778

Reaktionsgleichung

Reaktionsgleichung von HRID 57778
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.ClN1[C:18](=[O:19])[CH2:17][CH2:16]C1=O.C(O)C#C>C(N(CC)CC)C>[C:2]1([C:1]2[CH:16]=[C:17]([CH2:18][OH:19])[O:9][N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 7859Propargyl alcoholHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide2×

Produkt 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanolAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

10.0 mmol of Benzaldehyde oxime and 30 ml of dry dichloromethane were added into a 250 ml single-necked round-bottom flask. After the addition of 1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) under stirring, the mixture was slightly heated until NCS was completely dissolved. 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 ml solution of triethylamine in dichloromethane containing 10.1 g (10.0 mmol) of triethylamine was slowly added dropwise. 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 was separated on column (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield.

Aufarbeitung

  1. dissolutionwas completely dissolved
  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. customwas separated on column (Vpetroleum ether:Vethyl acetate=5:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3d742c6dc93b4aa08164691e7afb0562
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434741B2

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