Potassium Hydroxide → HCID 18687430, compound

HRID 1872691Notes

Reaction equation

HRID 1872691 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:18]2([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])(C(C)(C)C)(C)C.C(=O)(O)[O-:26].[Na+].[OH-].[K+].[Mn]([O-])(=O)(=O)=O.[K+]>CO.Cl>[CH3:17][O:16][C:15]1[CH:14]=[CH:13][C:12]([C:18]2([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]2)=[CH:11][C:10]=1[C:9]([OH:8])=[O:26]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 54490032HCID 54490032, compound

Product 1

HCID 18687430HCID 18687430, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[3 -(tert-butyldimethylsilanyloxymethyl)-4-methoxyphenyl]-3-trifluoromethyl-3H-diazirine (150 mg, 0.41 mmol) in methanol (5 ml) was stirred for 20 min with conc. HCl (2 drops). The solution was poured onto saturated aqueous sodium bicarbonate (10 ml) and extracted with dichloromethane (3×5 ml). The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure. The residue was taken up in dioxane (3 ml) and aqueous potassium hydroxide (2.5 ml of a 0.2M solution), potassium permanganate (98 mg, 0.62 mmol) was added and the mixture stirred for 4 h. The mixture was filtered through a pad of Celite and washed with water. The filtrate was extracted with ether (2×10 ml). The aqueous phase was brought to pH 1, extracted with ether (2×10 ml) and these extracts were dried over sodium sulfate and evaporated in vacuo to give the title compound (77 mg, 72%) as an off white solid.

Workup

  1. extractionextracted with dichloromethane (3×5 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. filtrationThe mixture was filtered through a pad of Celite
  5. washwashed with water
  6. extractionThe filtrate was extracted with ether (2×10 ml)
  7. extractionextracted with ether (2×10 ml)
  8. dry with materialthese extracts were dried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-47726ef5fcbf4f118e996ec495e9229d
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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