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

HRID 1251955노트

반응식

HRID 1251955 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8989ee64cd304c14ac06ae622aa16f92
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04741766

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