Water → HCID 23725856, compound

HRID 2219421Notes

Reaction equation

HRID 2219421 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[CH:15][N:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH:17]=1.[Li]CCCC.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35].O>C1COCC1>[CH2:37]([O:36][C:34]([C:15]1[N:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)[CH:17]=[C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])[N:14]=1)=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 23725748HCID 23725748, compoundHCID 178418339Butyllithium

Product 1

HCID 23725856HCID 23725856, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of 5-methyl-3-phenyl-4-[1-(4-trifluoromethyl-phenyl)-1H-imidazol-4-yl]-isoxazole (950 mg, 2.6 mmol) in THF (50 mL) at −78° C. was added BuLi (1.6 M in hexane, 2.4 mL, 3.9 mmol) and the resulting mixture allowed to warm up to −25° C. over 20 min and then re-cooled to −78° C. Then ethyl chloroformate (474 mg, 4.4 mmol) was added and the resulting mixture allowed to warm up to −25° C. over 3 h and then warmed up to 0° C. whereupon water was added. The reaction mixture was then extracted with ethyl acetate and the combined organic layers were then washed with a saturated solution of sodium hydrogen carbonate, brine and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (232 mg, 18%) which was obtained as an off-white foam. MS: m/e=442.5 [M+H]+.

Workup

  1. temperaturere-cooled to −78° C
  2. temperatureto warm up to −25° C. over 3 h
  3. additionwas added
  4. extractionThe reaction mixture was then extracted with ethyl acetate
  5. washthe combined organic layers were then washed with a saturated solution of sodium hydrogen carbonate, brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-5b22f1eb2d754e128a8b24726bdcfbb4
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

Loading…