Ethyl Acetate → HCID 19432440, compound

HRID 654645Notes

Reaction equation

HRID 654645 reaction equation
[CH3:1][Sn:2]([CH3:26])([CH3:25])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]3[CH:11]=[CH:12][C:13]([CH2:15][O:16][Si](C(C)(C)C)(C)C)=[CH:14][C:9]=3[O:8][C:7]=2[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].CCOC(C)=O>C1COCC1>[CH3:1][Sn:2]([CH3:26])([CH3:25])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]3[CH:11]=[CH:12][C:13]([CH2:15][OH:16])=[CH:14][C:9]=3[O:8][C:7]=2[CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 19437716HCID 19437716, compound

Product 1

HCID 19432440HCID 19432440, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the dibenzofuran 316 (339 mg, 0.71 mmol) in anhydrous THF (7 mL) at 0° C. under a nitrogen atmosphere was added dropwise a 1M solution of tetrabutylammonium fluoride in THF (0.92 mL, 0.92 mmol). The reaction solution was stirred for 30 min., then saturated ammonium chloride was added. The mixture was then extracted with EtOAc and the organic solution was washed with brine. The organic solution was then dried with magnesium sulfate and then filtered and concentrated under vacuum. Flash chromatography of the residue (silica gel, 25% EtOAc in hexanes) provided 182 mg of 317 (70% yield) as a white solid.

Workup

  1. extractionThe mixture was then extracted with EtOAc
  2. washthe organic solution was washed with brine
  3. dry with materialThe organic solution was then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b945395e81b48ad99edf64626096fbe
Source dataset
uspto-grants-1992_07
Patent number
US05132420

Reaction notes

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