Nitric Acid → HCID 58959917, compound

HRID 916016Notes

Reaction equation

HRID 916016 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:5][C:6]([OH:24])([CH2:11][C:12]([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13])[C:7]([F:10])([F:9])[F:8].[N+:33]([O-])([OH:35])=[O:34].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=1)[CH2:5][C:6]([OH:24])([CH2:11][C:12]([CH3:14])([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([N+:33]([O-:35])=[O:34])[CH:16]=1)[CH3:13])[C:7]([F:9])([F:8])[F:10]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 10195692HCID 10195692, compound

Product 1

HCID 58959917HCID 58959917, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 42 mg (0.087 mmol) of 2-(3-chloro-2-fluoro-5-trifluoromethylbenzyl)-4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol in 2 mL of acetic acid was added a mixture of 15 μL of fuming nitric acid (90%) and 22 μL of sulfuric acid in 250 μL of acetic acid in several portions. The mixture eventually turned from clear to green to deep blue. After 5 minutes, the reaction was cautiously made basic with saturated aqueous sodium bicarbonate and extracted with four 6 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate, two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The yellow residue was purified by preparative chromatography (silica gel, EtOAc-hexanes, (2:8)) to afford 34 mg of partially purified product, a second preparative chromatography (silica gel, toluene-hexanes (6:4)) afforded 24 mg of the title compound.

Workup

  1. extractionextracted with four 6 mL portions of EtOAc
  2. washThe combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate, two 5 mL portions of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe yellow residue was purified by preparative chromatography (silica gel, EtOAc-hexanes, (2:8))
  7. customto afford 34 mg of partially purified product

Sources & evidence

ORD record
ord-abc6abaf06724b44a10a912552f9072c
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

Loading…