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

HRID 255411
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인쇄 미리보기

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HRID 255411 반응식
[Li+].CC([N-]C(C)C)C.[F:9][C:10]([F:28])([F:27])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([Cl:22])[CH:14]=[C:13]([C:23]([F:26])([F:25])[F:24])[N:12]=1.[C:29](=[O:31])=[O:30].Cl>COCCOC.O>[F:28][C:10]([F:9])([F:27])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([Cl:22])[C:14]([C:29]([OH:31])=[O:30])=[C:13]([C:23]([F:24])([F:25])[F:26])[N:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

생성물 1

HCID 140137833-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-chloro-3,5-pyridinedicarboxylate수율 37.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 80711,2-Dimethoxyethane용매2회

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온도
-78 °C

실험 절차

To a -78° C. solution of LDA (0.128 mol) in 85 ml of DME was added a solution of 18.28 g (0.057 mol) of product of Example 9 in 20 ml of DME. The reaction mixture was stirred at -78° C. for 1 hour. To the above solution was added excess of dry ice. After stirring at -78° C. the reaction mixture was warmed to room temperature in 1 hour and poured into 250 ml of water containing 50 ml of concentrated HCl. The oil precipitate was extracted into ether. The ether extract was extracted with saturated NaHCO3. The basic extract was made acidic with concentrated HCl. The oil precipitate was extracted into ether. The ether solution was dried (MgSO4) and concentrated in vacuo to give 7.81 g (37.6%) of product as a solid; mp 113°-115° C.

후처리

  1. stirringAfter stirring at -78° C. the reaction mixture
  2. temperaturewas warmed to room temperature in 1 hour
  3. extractionThe oil precipitate was extracted into ether
  4. extractionThe ether extract
  5. extractionwas extracted with saturated NaHCO3
  6. extractionThe basic extract
  7. extractionThe oil precipitate was extracted into ether
  8. dry with materialThe ether solution was dried (MgSO4)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-66c25f1dc98e4f5f80fa1188859f4ce9
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04698093

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