Sodium Bicarbonate → 4-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butan-1-ol

HRID 1245339Notes

Reaction equation

HRID 1245339 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:25]=[CH:24][C:16]2[C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][O:19][C:15]=2[C:14]=1[CH2:26][CH2:27][CH3:28])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:26]([C:14]1[C:15]2[O:19][N:18]=[C:17]([C:20]([F:21])([F:23])[F:22])[C:16]=2[CH:24]=[CH:25][C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 219110176-(4-{[Tert-butyl(dimethyl)silyl]oxy}butyl)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole

Product 1

HCID 219110454-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole, from this Example step 3, (2.8 g, 6.7 mmol) in dry THF (75 mL) was added tetrabutylammonium fluoride (1.0M 10.1 mL, 10.1 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours. Saturated NaHCO3 was added and the mixture was extracted with ethyl acetate 3 times. Combined organic extracts were washed with brine and dried over Na2SO4. The solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate and hexane (20:80) to give the title compound.

Workup

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate 3 times
  3. washCombined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-01aeee141ecc4473a7ecfc5afdaeb0d4
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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