Ethyl Glycolate → HCID 71239586、化合物

HRID 1508193ノート

反応式

HRID 1508193 の反応式
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].C([O:12][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[N:17][C:16]=1Cl)=O)C>COCCOC>[CH2:8]([O:7][C:3]([C:4]1[O:5][C:16]2[N:17]=[N:18][CH:19]=[CH:20][C:15]=2[C:13]=1[OH:12])=[O:6])[CH3:9]

参加物

5

反応物 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 14542887Ethyl 3-chloropyridazine-4-carboxylate

生成物 1

HCID 71239586HCID 71239586、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
75 °C

実験手順

To a suspension of NaH (44.7 mmol) in 100 mL 1,2-dimethoxyethane was added ethyl glycolate (43 mmol) under ice cooling and stirring. The ice bath was removed and stirring was continued at RT. After 30 min, a solution of 3-chloropyridazine-4-carboxylic acid ethyl ester (17.2 mmol) in 40 mL 1,2-dimethoxyethane was slowly added and the mixture was heated to 75° C. for 2 h. The solvent was then evaporated off and the residual solid was redissolved in aq. NaHCO3 solution and EtOAc. The aqueous layer was acidified with AcOH and extracted with DCM (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using EtOAc/MeOH (1/1) gives the desired product as brown solid;

後処理

  1. customThe ice bath was removed
  2. stirringstirring
  3. customwas continued at RT
  4. customThe solvent was then evaporated off
  5. dissolutionthe residual solid was redissolved in aq. NaHCO3 solution
  6. extractionextracted with DCM (3×)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification by CC (KP-SIL™ from Biotage)

出典と根拠

ORDレコード
ord-547e2086c6464ec6985a611b37d17359
出典データセット
uspto-grants-2015_12
特許番号
US09221832B2

反応ノート

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