Ethyl Acetate → Diphenyl Ether

HRID 993460Notes

Reaction equation

HRID 993460 reaction equation
C(NCC[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=O)CC.[H-].[Na+].C(O[CH2:21][CH3:22])(=O)C>O1CCCC1>[C:22]1([O:14][C:11]2[CH:10]=[CH:9][CH:8]=[CH:13][CH:12]=2)[CH:21]=[CH:10][CH:9]=[CH:8][CH:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14717710N-[2-(4-Hydroxyphenyl)ethyl]propanamide

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-bdfcae41887a4621b017c52e345cd51c
Source dataset
uspto-grants-2002_10
Patent number
US06472387B1

Reaction notes

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