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

HRID 1378399노트

반응식

HRID 1378399 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e00ee011f41042b1923bb2b9aa02b9c0
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668146

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