Ethyl Acetate → Diphenyl Ether

HRID 1276962Notes

Reaction equation

HRID 1276962 reaction equation
C(N(C(=O)CC)CC[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)C.[H-].[Na+].C(O[CH2:23][CH3:24])(=O)C>O1CCCC1>[C:24]1([O:12][C:9]2[CH:8]=[CH:7][CH:6]=[CH:11][CH:10]=2)[CH:23]=[CH:8][CH:7]=[CH:6][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69946721HCID 69946721, compound

Product 1

HCID 7583Diphenyl EtherYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-ethyl,N-propionyl tyramine (2.84 g, 12.83 mmole) in tetrahydrofuran (32.1 ml) was added 60% sodium hydride dispersion (0.56 g, 14.11 mmole). After stirring for 10 minutes, the compound of Example 42(E) (4.70 g, 12.83 mmole) was added. The reaction was allowed to stir at room temperature for 5 hours, poured into ethyl acetate, and extracted with 10% sodium sulfate, then brine. The organic layer was dried over sodium sulfate, evaporated to dryness, and chromatographed on silica gel using a hexane-ethyl acetate gradient. Further chromatography on silica gel using toluene-acetone gradients yielded the intermediate phenyl ether (2.10 g, 32%):

Workup

  1. stirringto stir at room temperature for 5 hours
  2. extractionextracted with 10% sodium sulfate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customchromatographed on silica gel using a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-d9da7c0080914e198eb58a0443531f44
Source dataset
uspto-grants-2000_12
Patent number
US06166216

Reaction notes

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