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

HRID 255407
ノート
印刷プレビュー

反応式

HRID 255407 の反応式
[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
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

5

反応物 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamide2 回HCID 13882869Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3-pyridinecarboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane
溶媒
2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b5a2b9fcd304fdb97d43041264673c0
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04698093

反応ノート

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