Triacetoxyperiodinane → 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazole-7-carbaldehyde

HRID 1506431Notes

Reaction equation

HRID 1506431 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[C:20]4[CH2:21][O:22][C:23]5[CH:24]=[C:25]([CH2:29][OH:30])[CH:26]=[CH:27][C:28]=5[C:19]=4[O:18][N:17]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[C:20]4[CH2:21][O:22][C:23]5[CH:24]=[C:25]([CH:29]=[O:30])[CH:26]=[CH:27][C:28]=5[C:19]=4[O:18][N:17]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67169318(3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanol

Product 1

HCID 866699043-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazole-7-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanol (Preparation 60H, 0.027 g, 0.065 mmol) in dichloromethane (2.0 mL) at room temperature was added Dess-Martin Periodinane (0.030 g, 0.072 mmol). The reaction mixture was stirred for 30 min. The reaction was quenched with a 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate (˜2.0 mL), extracted with dichloromethane (2×), and the combined organic layers were dried over anhydrous sodium sulfate and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazole-7-carbaldehyde (0.027 g, 0.065 mmol, 100% yield) as a white solid. The product had an HPLC ret. time=3.31 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA.

Workup

  1. customThe reaction was quenched with a 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate (˜2.0 mL)
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered through a pad of Celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-40da4ea0e9fe405f9c46a31b8847310a
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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