Acetonitrile → 3-Formyl-8-(2-(cis)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

HRID 1195735ノート

反応式

HRID 1195735 の反応式
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][C@H:14]3[O:22]S(C)(=O)=O)[C:6]2=[N:5][C:4]=1[CH3:27])=[O:2].C([O-])(=O)C.[K+].O1CCOCCOCCOCCOCCOCC1.C(#N)C>ClCCl>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][C@@H:14]3[OH:22])[C:6]2=[N:5][C:4]=1[CH3:27])=[O:2]

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 228438343-Formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

生成物 1

HCID 228438353-Formyl-8-(2-(cis)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine収率 14.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

1 g of 3-formyl-2-methyl-8-(2-(trans)-methylsulfonyloxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine is added to a mixture of 5.1 g of anhydrous potassium acetate, 13.8 g of 1,4,7,10,13,16-hexaoxacyclooctadecan ("18-crown-6) and 100 ml of anhydrous acetonitrile, while stirring and excluding any moisture. The brownish suspension is warmed for 18 hours at 70° C. and heated for a further 10 hours under reflux. After cooling, it is poured onto water and extraction carried out several times with dichloromethane. The organic phases are washed with water, dried and the solvent stripped off in vacuo. The dark brown residue is assayed by chromotography with the mobile phase ethyl acetate/methanol=95:5 (V/V) over silica gel. After stripping off of the solvent, the residue (0.18 g) is dissolved in 3.6 ml methanol and this solution is added dropwise with stirring to a solution of 0.072 g potassium hydroxide in 1.2 ml water. Stirring continues for one hour at room temperature, water is added, the pH is adjusted with diluted acetic acid to 6 and extraction is carried out several times with dichloromethane. The organic phases are washed with water, dried and the solvent is stripped off in vacuo. 115 mg of the title compound as a yellowish residue of m.p. 171°-173° C. is obtained.

後処理

  1. temperatureheated for a further 10 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. additionit is poured onto water and extraction
  5. washThe organic phases are washed with water
  6. customdried
  7. dissolutionthe residue (0.18 g) is dissolved in 3.6 ml methanol
  8. additionthis solution is added dropwise
  9. stirringwith stirring to a solution of 0.072 g potassium hydroxide in 1.2 ml water
  10. stirringStirring
  11. additionwater is added
  12. extractionthe pH is adjusted with diluted acetic acid to 6 and extraction
  13. washThe organic phases are washed with water
  14. customdried

出典と根拠

ORDレコード
ord-88ae952e3fc94e0f87eed499949aa753
出典データセット
uspto-grants-1992_05
特許番号
US05112834

反応ノート

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