Ethylparaben → Ethyl 4-(2-pyrazinylmethoxy)benzoate

HRID 1460204노트

반응식

HRID 1460204 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-342fbf2c838c49a8a2f9ac999be3a679
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05070090

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