Citric Acid → 1,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanol

HRID 1378399ノート

反応式

HRID 1378399 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](=[O:42])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:26][CH:25]=2)=[CH:15][CH:14]=1.C(O)C.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]([OH:42])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)=[CH:26][CH:25]=2)=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 107928071,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone

生成物 1

HCID 105069561,5-Bis(4-(2-quinolylmethoxy)phenyl)-3-pentanol収率 103.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1,5-bis(4-(2-quinolylmethoxy)phenyl)-3-pentanone (2.21 g, 4 mmol), prepared as in step 3, in dioxane (15 mL) and ethanol (35 mL) was added NaBH4 (152 mg, 4 mmol) and the resulting mixture was refluxed for 30 minutes. The solution was then cooled to room temperature, acidified to pH 5 with 10% citric acid and concentrated in vacuo. To the residue was added water (50 mL) and the precipitated solid was filtered to afford 1,5-bis(4-(2-quinolylmethoxy)phenyl)-3-pentanol (2.3 g).

後処理

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. concentrationconcentrated in vacuo
  3. additionTo the residue was added water (50 mL)
  4. filtrationthe precipitated solid was filtered

出典と根拠

ORDレコード
ord-e00ee011f41042b1923bb2b9aa02b9c0
出典データセット
uspto-grants-1997_09
特許番号
US05668146

反応ノート

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