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

HRID 2291470
ノート
印刷プレビュー

反応式

HRID 2291470 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f8ee972e1ba040d6bbe47d65c9c4ff49
出典データセット
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04797149

反応ノート

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