Potassium Carbonate → HCID 66955572, compound

HRID 2066643Notes

Reaction equation

HRID 2066643 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Cl:13][C:14]1[N:15]([CH2:22][CH2:23][CH:24]2[CH2:26][O:25]2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC.O>[Cl:13][C:14]1[N:15]([CH2:22][CH2:23][CH:24]([OH:25])[CH2:26][O:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[N:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 86650544HCID 86650544, compound

Product 1

HCID 66955572HCID 66955572, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
81 °C

Procedure

4-Trifluoromethoxyphenol (0.375 mL, 2.89 mmol) was added to a mixture of epoxide 129 (250 mg, 1.15 mmol) and powdered K2CO3 (558 mg, 4.04 mmol) in anhydrous 2-butanone (3 mL) under N2, and the mixture was stirred at 81° C. for 12 h. The resulting cooled mixture was diluted with water (50 mL) and extracted with CH2Cl2 (4×50 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-25% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 25-33% EtOAc/petroleum ether gave 4-(2-chloro-4-nitro-1H-imidazol-1-yl)-1-[4-(trifluoromethoxy)phenoxy]-2-butanol (130) (306 mg, 67%) as a pale yellow oil; 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.16 (br dd, J=9.1, 0.8 Hz, 2H), 6.88 (dt, J=9.2, 3.0 Hz, 2H), 4.37-4.24 (m, 2H), 4.02-3.93 (m, 2H), 3.86 (dd, J=10.0, 7.8 Hz, 1H), 2.47 (dd, J=4.2, 1.1 Hz, 1H), 2.13-1.98 (m, 2H); HRESIMS calcd for C14H14ClF3N3O3 m/z [M+H]+ 398.0540, 396.0569. found 398.0538, 396.0567.

Workup

  1. temperatureThe resulting cooled mixture
  2. extractionextracted with CH2Cl2 (4×50 mL)
  3. customThe extracts were evaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 0-25% EtOAc/petroleum ether firstly gave foreruns
  6. washfurther elution with 25-33% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-ec9b7f9ff851424cbd16d4824d9e7dee
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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