Water → Diethyl 2,4-diisopropoxy-6-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 64570ノート

反応式

HRID 64570 の反応式
[Li+].CC([N-]C(C)C)C.[CH:9]([O:12][C:13]1[CH:18]=[C:17]([O:19][CH:20]([CH3:22])[CH3:21])[N:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[C:14]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:11])[CH3:10].Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34].O>COCCOC>[CH:20]([O:19][C:17]1[C:18]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:13]([O:12][CH:9]([CH3:10])[CH3:11])[C:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:15]([C:23]([F:24])([F:26])[F:25])[N:16]=1)([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 2724682Lithium diisopropylamideHCID 13726788Ethyl 4,6-diisopropoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

生成物 1

HCID 13726801Diethyl 2,4-diisopropoxy-6-(trifluoromethyl)-3,5-pyridinedicarboxylate収率 34.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a -78° C. solution of 0.021 mol of LDA in DME (30 ml) was added a solution of 4.65 g (0.014 mol) of product of Example 6 in 20 ml of DME. The resulting solution was stirred for 10 minutes and treated with 2.7 ml (0.035 mol) of ethyl chloroformate. After stirring at -78° C. for 30 minutes the reaction mixture was warmed to room temperature in 30 minutes and poured into 50 ml of water. The mixture was extracted with ether. The ether extract was washed with 10% K2CO3, dried over CaSO4 and concentrated. The residue was first kugelrohr distilled at 0.15 torr (pot temperature 55° C.) to remove low boiling material (1.08 g), then distilled at 164°-173° C. (0.15 torr) to give 1.95 g (34.5%) of product as an oil.

後処理

  1. stirringAfter stirring at -78° C. for 30 minutes the reaction mixture
  2. extractionThe mixture was extracted with ether
  3. extractionThe ether extract
  4. washwas washed with 10% K2CO3
  5. dry with materialdried over CaSO4
  6. concentrationconcentrated
  7. distillationdistilled at 0.15 torr (pot temperature 55° C.)
  8. customto remove low boiling material (1.08 g)
  9. distillationdistilled at 164°-173° C. (0.15 torr)

出典と根拠

ORDレコード
ord-ea6929a300ef40f88e9a6aec6f60e869
出典データセット
uspto-grants-1986_09
特許番号
US04609399

反応ノート

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