Methanol → HCID 21866692, compound

HRID 857230Notes

Reaction equation

HRID 857230 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]([C:17]([F:20])([F:19])[F:18])=[C:10]([CH2:12][CH2:13][CH2:14][C:15]#N)[N:11]=2)=[CH:3][CH:2]=1.[OH2:22].[CH3:23][OH:24]>>[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]([C:17]([F:20])([F:19])[F:18])=[C:10]([CH2:12][CH2:13][CH2:14][C:15]([O:24][CH3:23])=[O:22])[N:11]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 962Water2×HCID 21866633HCID 21866633, compound

Product 1

HCID 21866692HCID 21866692, compound

Procedure

4-[2-(p-Tolyl)-5-trifluoromethyloxazol-4-yl]butanenitrile (5.28 g) was dissolved in 40 ml of methanol, and stirred for 10 minutes under ice-cooling under bubbling hydrogen chloride gas. After the bubbling was stopped, the mixture was warmed to room temperature and stirred for 30 minutes. To the reaction solution was added 5 ml of water, and the mixture was stirred for 30 minutes, allowed to stand at room temperature overnight. After addition of water, the reaction solution was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1) to provide 5.63 g of the objective compound as colorless crystals. M.p. 44.5-45° C.

Workup

  1. temperaturecooling under bubbling hydrogen chloride gas
  2. stirringstirred for 30 minutes
  3. stirringthe mixture was stirred for 30 minutes
  4. waitto stand at room temperature overnight
  5. extractionthe reaction solution was extracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3422e09d66f84a04abacc56ae486c377
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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