Ethylparaben → Ethyl 4-(2-pyrazinylmethoxy)benzoate

HRID 1460204Notes

Reaction equation

HRID 1460204 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][OH:8].O[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7][O:8][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 201734PyrazinemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 19983178Ethyl 4-(2-pyrazinylmethoxy)benzoateYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (≤5° C.) solution of 8.3 parts of 2-pyrazinemethanol, 13.3 parts of ethyl 4-hydroxybenzoate and 20.2 parts of triphenylphosphine in 178 parts of tetrahydrofuran was added dropwise a solution of 13.93 parts of diethyl azodicarboxylate in 45 parts of tetrahydrofuran. Upon completion, the reaction mixture was stirred over weekend. After evaporation, the residue was taken up in water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in 2,2'-oxybispropane. The precipitate was filtered off and the filtrate was evaporated. The residue was crystallized from 2-propanol, yielding 7.5 parts (38.7%) of ethyl 4-(2-pyrazinylmethoxy)benzoate; mp. 76.1° C. (interm. 9).

Workup

  1. stirringUpon completion, the reaction mixture was stirred over weekend
  2. customAfter evaporation
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue was stirred in 2,2'-oxybispropane
  8. filtrationThe precipitate was filtered off
  9. customthe filtrate was evaporated
  10. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-342fbf2c838c49a8a2f9ac999be3a679
Source dataset
uspto-grants-1991_12
Patent number
US05070090

Reaction notes

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