Hydrochloric Acid → HCID 21105765, compound

HRID 1354423Notes

Reaction equation

HRID 1354423 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:21]([O:28][C:29]1[CH:44]=[CH:43][C:42](I)=[CH:41][C:30]=1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH2:21]([O:28][C:29]1[CH:44]=[CH:43][C:42]([C:11]2[O:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:8][CH:7]=3)=[CH:13][CH:12]=2)=[CH:41][C:30]=1[C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 106561512-(4-Trifluoromethylphenyl)furanHCID 22934559HCID 22934559, compoundHCID 178418339Butyllithium

Product 1

HCID 21105765HCID 21105765, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (25 ml) of 2-(4-trifluoromethylphenyl)furan (3.18 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 10.0 ml) under an argon atmosphere at −78° C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.25 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and benzyl 2-benzyloxy-5-iodobenzoate (6.66 g) and tetrakis (triphenylphosphine)palladium (0.433 g) were added. This mixture was stirred overnight under an argon atmosphere, and poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1, volume ratio) and recrystallized from hexane-ethyl acetate to give benzyl 2-benzyloxy-5-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (3.41 g, yield 43%) as pale-yellow needle crystals. melting point: 97–98° C.

Workup

  1. stirringThis mixture was stirred overnight under an argon atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1, volume ratio)
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c619513b6b8f463e8595bf5d5386c4a3
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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