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Carbon Dioxide → 3-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

HRID 255407
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인쇄 미리보기

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HRID 255407 반응식
[Li+].CC([N-]C(C)C)C.[F:9][C:10]([F:30])([F:29])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1.[C:31](=[O:33])=[O:32]>COCCOC>[F:30][C:10]([F:29])([F:9])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[C:14]([C:31]([OH:33])=[O:32])=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1
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참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamide2회HCID 13882869Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3-pyridinecarboxylate2회

생성물 1

HCID 140137533-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate수율 52.7%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane
용매
2회

반응 조건

온도
-78 °C

실험 절차

This material was prepared in 52.7% yield from 0.06 mol of LDA and 0.024 mol of product of Example 6 according to the following general procedure as a beige solid, mp 115°-117° C. To a -78° C. solution of 2.5 eq (0.06 mol) of LDA in DME was added a solution of 1 eq (0.024 mol) of starting material, the monocarboxylate product (Example 6) in dry DME. The resulting dark colored solution was stirred for 30 minutes at -78° C. To the above solution was added excess of dry ice. The reaction mixture was stirred at -78° C. for 15 minutes and warmed to room temperature in 1 hour. The reaction mixture was poured into ice water (100 ml) and extracted with ether. The aqueous layer was made acidic. The oil precipitate was extracted with ether. The ether extract was dried (MgSO4) and concentrated in vacuo to give the desired product.

후처리

  1. stirringThe reaction mixture was stirred at -78° C. for 15 minutes
  2. temperaturewarmed to room temperature in 1 hour
  3. extractionextracted with ether
  4. extractionThe oil precipitate was extracted with ether
  5. extractionThe ether extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9b5a2b9fcd304fdb97d43041264673c0
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04698093

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