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

HRID 257260ノート

反応式

HRID 257260 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bcc0f057a1e441a7a2033d82d6d91e18
出典データセット
uspto-grants-1993_11
特許番号
US05260285

反応ノート

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