Ethanol → 9-((5-Hydroxypentyl)aminomethyl)anthracene

HRID 429705

反応式

HRID 429705 の反応式
[C:1]1(C=O)[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].[BH4-].[Na+].[CH2:26](O)C>>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][CH2:26][C:6]1[C:5]2[C:14]([CH:13]=[C:12]3[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]3)=[CH:1][CH:2]=[CH:3][CH:4]=2

参加物

5

反応物 4

HCID 702EthanolHCID 35864AnthracenecarboxaldehydeHCID 756345-Aminopentan-1-olHCID 4311764Sodium borohydride

生成物 1

HCID 108809079-((5-Hydroxypentyl)aminomethyl)anthracene収率 89.2%

実験手順

A solution of anthraldehyde (9.595 g, 0.0465 mol) and 5-amino-1-pentanol (15.00 g, 0.116 mol) dissolved in 500 mL ethanol at 0° C. was stiffed for 3 h. After warming to room temperature the solvent was removed under reduced pressure, and 150 mL of ethanol containing NaBH4 (4.65 g, 0.1229 mol) was added slowly with stirring. The resulting mixture was allowed to stir overnight. The ethanol was removed under reduced pressure and to the brown oil/solid mixture was added 150 mL diethyl ether. Water was added dropwise to this solution until the evolution of hydrogen ceased, followed by the addition of 500 mL water. The ether phase was isolated, washed with 2×50 mL water, dried over sodium sulfate and filtered on a sintered-glass frit. Removal of the solvent afforded 12.17 g (89.2% yield) of 5 as a golden solid; 1H NMR (300.13 MHz, CD3CN) δ1.51 (m, 6H), 2.81 (t, 2H), 3.49 (t, 2H), 4.68 (s, 2H), 7.52 (m, 4H), 8.05 (d, 2H), 8.44 (m, 3H); 13C-{1H} NMR (75.4 MHz, CDCl3) δ133.1, 132.0, 131.7, 130.4, 128.6, 127.4, 126.2, 125.1, 62.9, 51.1, 45.8, 33.5, 30.3, 24.8.

後処理

  1. customwas removed under reduced pressure, and 150 mL of ethanol
  2. additionwas added slowly
  3. stirringto stir overnight
  4. customThe ethanol was removed under reduced pressure and to the brown oil/solid mixture
  5. additionwas added 150 mL diethyl ether
  6. additionWater was added dropwise to this solution until the evolution of hydrogen
  7. additionfollowed by the addition of 500 mL water
  8. customThe ether phase was isolated
  9. washwashed with 2×50 mL water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered on a sintered-glass frit
  12. customRemoval of the solvent

出典と根拠

ORDレコード
ord-0d5f4d73b545455e91be7e1679ad22aa
出典データセット
uspto-grants-2001_11
特許番号
US06319540B1

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