Ethyl Acetate → (1,2,3,4-Tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-yl)methanol

HRID 1498896ノート

反応式

HRID 1498896 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[N:12]2[C:13]3[CH:19]=[CH:18][C:17]([C:20](OCC)=[O:21])=[CH:16][C:14]=3[N:15]=[C:11]2[CH2:10][CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH2:7]1[N:12]2[C:13]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:14]=3[N:15]=[C:11]2[CH2:10][CH2:9][CH2:8]1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12493647Ethyl 1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole-7-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 56598510(1,2,3,4-Tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-yl)methanol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminum hydride (1.97 g, 51.9 mmol) was suspended in tetrahydrofuran (30 ml); and under an ice cooling, a solution (20 ml) of ethyl 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-carboxylate (6.34 g, 26.0 mmol) prepared in the Step 3-1-3 in tetrahydrofuran was slowly added thereto. After the mixture was stirred under an ice cooling for one hour, a saturated sodium bicarbonate solution (5 ml) was slowly added to the mixture at the same temperature while paying attention to the generation of heat. Further, ethyl acetate was slowly added to the mixture. The mixture was allowed to cool to a room temperature and filtered. The filtrate was thoroughly washed with chloroform. The filtrate was concentrated and purified by silica gel column chromatography (chloroform:methanol=20:1 to 10:1) to give the title compound (4.20 g, 80%) as a white powder.

後処理

  1. additionwas slowly added
  2. temperatureof heat
  3. filtrationfiltered
  4. washThe filtrate was thoroughly washed with chloroform
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography (chloroform:methanol=20:1 to 10:1)

出典と根拠

ORDレコード
ord-033e2211808241ac89679e8e9ccb00c1
出典データセット
uspto-grants-2015_12
特許番号
US09200008B2

反応ノート

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