Hydroxyamine hydrochloride → HCID 4979911, compound

HRID 2364963Notes

Reaction equation

HRID 2364963 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:13][N:12]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:10]=1.FC(F)(F)C(=O)CC(C1C=CC=CC=1OC)=O.Cl.NO>C(O)C>[F:17][C:14]([F:15])([F:16])[C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[O:13][N:12]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 27714734,4,4-trifluoro-1-(2-methoxyphenyl)butane-1,3-dioneHCID 68380288HCID 68380288, compound

Product 1

HCID 4979911HCID 4979911, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesis of 5-(2-methoxyphenyl)-3-(trifluoromethyl)-1,2-oxazole (C10) A mixture of 4,4,4-trifluoro-1-(2-methoxyphenyl)butane-1,3-dione (C9) (933 mg, 3.79 mmol) and hydroxylamine hydrochloride (798 mg, 11.4 mmol) in ethanol (10 mL) was refluxed under nitrogen for 3 hours, then cooled to room temperature. The reaction was concentrated in vacuo, treated with water (30 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptanes) afforded the title compound as a yellow oil. Yield: 502 mg, 2.06 mmol, 54%. GCMS m/z 243 (M+). 1H NMR (400 MHz, CDCl3) δ 4.00 (s, 3H), 7.01 (s, 1H), 7.05 (dd, J=8.4, 0.9 Hz, 1H), 7.11 (ddd, J=7.8, 7.4, 1.1 Hz, 1H), 7.48 (ddd, J=8.4, 7.4, 1.8 Hz, 1H), 8.00 (dd, J=7.8, 1.7 Hz, 1H).

Workup

  1. temperaturewas refluxed under nitrogen for 3 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. additiontreated with water (30 mL)
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-a0f4e0ef951b48d7ac5b8d563535e5b3
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

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