Diethyl Ether → 959617-20-0

HRID 385586Notes

Reaction equation

HRID 385586 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[C:8]([CH2:11][OH:12])[CH:7]=2)=[CH:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C>ClCCl>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[C:8]([CH:11]=[O:12])[CH:7]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087Triacetoxyperiodinane2×HCID 57815492HCID 57815492, compound

Product 1

HCID 57815525959617-20-0Yield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 mg of (5-(3-thienyl)isoxazol-3-yl)methanol in 5 mL of dichloromethane, 84 mg of Dess-Martin periodinane was added under cooling with ice, and the mixture was stirred at room temperature for 1 hour 30 minutes. Thereto was further added 40 mg of Dess-Martin periodinane, and the mixture was stirred at room temperature for 1 hour 30 minutes. Diethyl ether was added to the reaction mixture, the insoluble substance was filtered off, and the solvent was distilled off under reduced pressure to obtain 30 mg of 5-(3-thienyl)isoxazole-3-carbaldehyde as a yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 1 hour 30 minutes
  3. filtrationthe insoluble substance was filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-76982cfec3ec4f7fbf87344ca0eedfad
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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