Bicarbonate Ion → 1-(3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanone

HRID 1506543Notes

Reaction equation

HRID 1506543 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]([OH:27])[CH3:26])=[CH:19][CH:18]=5)[C:8]=2[C:28]([F:31])([F:30])[F:29])[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.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-]>ClCCl>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([C:25](=[O:27])[CH3:26])=[CH:19][CH:18]=5)[C:8]=2[C:28]([F:29])([F:30])[F:31])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 671719831-(3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanol

Product 1

HCID 671715271-(3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanol (Preparation 125A 0.44 g, 1.032 mmol) in dichloromethane (5 mL) was added Dess-Martin Periodinane (0.481 g, 1.135 mmol) in batches, over 2 min. at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. A 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous bicarbonate (3.6 mL) was added slowly to the reaction mixture at room temperature and the contents stirred for 15 min. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic layers were dried over sodium sulfate, filtered through a pad of Celite and concentrated under reduce pressure to yield 1-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethanone (0.415 g, 0.978 mmol, 95% yield) as a tan colored solid. LC/MS M+1=425.

Workup

  1. additionwas added slowly to the reaction mixture at room temperature
  2. stirringthe contents stirred for 15 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-969e03e3f2f44ee08be4d2555b092c08
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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