Water → 6-[(Diethylamino)methyl]-2-naphthalenemethanol

HRID 1636379노트

반응식

HRID 1636379 반응식
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16](O)=[O:17])[CH:10]=[CH:9]2)=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([N:3]([CH2:4][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16][OH:17])[CH:10]=[CH:9]2)[CH2:19][CH3:20])[CH3:2]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 193511076-(Diethylaminocarbonyl)-2-naphthalenecarboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 193511506-[(Diethylamino)methyl]-2-naphthalenemethanol수율 79.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 6-(diethylaminocarbonyl)-2- naphthalenecarboxylic acid (18 g, 66 mmol) in THF (200 ml) was slowly added to a refluxing suspension of lithium aluminium hydride (7.5 g, 199 mmol) in THF (500 ml). The mixture was refluxed for an hour, then cooled at room temperature and treated with a mixture of THF (25 ml) and water (3.5 ml), with 20% sodium hydroxide (8.5 ml) and finally with water (33 ml). The white solid was filtered off and the solvent was removed under reduced pressure. Crude was dissolved in diethyl ether (200 ml) and extracted with 1N HCl (3×100 ml). The aqueous solution was treated with 32% sodium hydroxide and extracted with diethyl ether (3×100 ml). The organic solution was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure yielding 12.7 g (79% yield) of pure 6-(diethylaminomethyl)-2-naphthalenemethanol as thick oil.

후처리

  1. temperatureThe mixture was refluxed for an hour
  2. filtrationThe white solid was filtered off
  3. customthe solvent was removed under reduced pressure
  4. dissolutionCrude was dissolved in diethyl ether (200 ml)
  5. extractionextracted with 1N HCl (3×100 ml)
  6. additionThe aqueous solution was treated with 32% sodium hydroxide
  7. extractionextracted with diethyl ether (3×100 ml)
  8. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  9. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-4addbdb9373345108566cde4ef6afd79
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06034096

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