Sodium Bicarbonate → (1-methyl-1H-benzo[d]imidazol-5-yl)methanol

HRID 1498891

反応式

HRID 1498891 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17](OCC)=[O:18])=[CH:16][C:11]=2[N:10]=[CH:9]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:11]=2[N:10]=[CH:9]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 965320Ethyl 1-methyl-1h-benzimidazole-5-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 14518388(1-methyl-1H-benzo[d]imidazol-5-yl)methanol収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an argon gas flow, lithium aluminum hydride (9.70 g, 256 mmol) was suspended in tetrahydrofuran (100 ml); and under an ice cooling, a solution (100 ml) of ethyl 1-methyl-1H-benzimidazole-5-carboxylate (26.1 g, 128 mmol) prepared in the Step 1-1-4 in tetrahydrofuran was slowly added thereto. The mixture was stirred under an ice cooling for one hour. Under an ice cooling, a saturated sodium bicarbonate solution was slowly added to the mixture. The precipitate was removed by filtration, and the residue was concentrated. The concentrate was dissolved in chloroform, and the solution was washed with a saturated sodium bicarbonate solution and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1 to 5:1) to give the title compound (11.4 g, 55%) as a light-red powder.

後処理

  1. additionwas slowly added
  2. customThe precipitate was removed by filtration
  3. concentrationthe residue was concentrated
  4. dissolutionThe concentrate was dissolved in chloroform
  5. washthe solution was washed with a saturated sodium bicarbonate solution
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1 to 5:1)

出典と根拠

ORDレコード
ord-58975c674d82430db184610335272468
出典データセット
uspto-grants-2015_12
特許番号
US09200008B2

関連ノート

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