Ethyl acetate hexane → 2-Ethyl-6,8-dimethyl-3-hydroxymethylimidazo[1,2-b]pyridazine

HRID 257260노트

반응식

HRID 257260 반응식
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[C:14](OCC)=[O:15])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.CCCCCC>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][OH:15])[CH3:2]

참가 물질

5

반응물 3

HCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 53827167Ethyl (2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)carboxylate

생성물 1

HCID 197841432-Ethyl-6,8-dimethyl-3-hydroxymethylimidazo[1,2-b]pyridazine수율 84.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2.702 g (10.9 mmol) of the product of Step A dissolved in 21 mL of anhydrous THF was added 6.0 mL of a 1.0M solution of lithium aluminum hydride in THF at 0° C., and the reaction mixture was stirred under a nitrogen atmosphere. After 1 hour TLC analysis (75% EtOAc-hexane) indicated complete reduction of the ester, and the reaction mixture was quenched by stepwise addition of 0.23 mL water, 0.23 mL of 15% sodium hydroxide solution, and finally 0.69 mL of water. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residual oil was redissolved in EtOAc and dried (MgSO4), filtered, evaporated and dried in vacuo to afford 1.884 g (84%) of a tan solid which was used in the next step without further purification.

후처리

  1. customreduction of the ester, and the reaction mixture was quenched by stepwise addition of 0.23 mL water, 0.23 mL of 15% sodium hydroxide solution, and finally 0.69 mL of water
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residual oil was redissolved in EtOAc
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-bcc0f057a1e441a7a2033d82d6d91e18
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260285

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