Heptanol → 6-(Heptyloxy)-7H-purine

HRID 1978802ノート

反応式

HRID 1978802 の反応式
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].Cl[C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2>O1CCCC1>[CH2:1]([O:8][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[NH:14][CH:15]=[N:16]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

5

反応物 3

HCID 8129HeptanolHCID 24758Sodium hydrideHCID 53592776-Chloropurine

生成物 1

HCID 212011806-(Heptyloxy)-7H-purine収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Heptanol (45.02 g, 0.388 mol) was added to a stirred suspension of a 60% dispersion of sodium hydride in oil (16.62 g, 0.416 mol) in dry tetrahydrofuran (350 ml) under an atmosphere of nitrogen. After gas evolution had ceased (about 1 h), 6-chloropurine (16.04 g, 0.104 mol) was added. The reaction began to foam and more gas was evolved. When gas evolution had ceased (about 0.75 h) the reaction was heated at reflux for 3 h then the solvent was removed in vacuo. The residual oily solid was suspended in water (2l) then concentrated hydrochloric acid (30 ml) was added. The aqueous suspension was neutralised with saturated sodium hydrogen carbonate solution and 60-80 petroleum ether (750 ml) added. The solid was moved from the biphasic mixture by filtration, washed with 60-80 petroleum ether and dried at oil-pump vacuum/40° C. This gave the title compound (1)(18.64 g, 79.7 mmol, 77%) as a white solid.

後処理

  1. additionwas added
  2. custom(about 0.75 h)
  3. temperaturewas heated
  4. temperatureat reflux for 3 h
  5. customthe solvent was removed in vacuo
  6. additionconcentrated hydrochloric acid (30 ml) was added
  7. additionadded
  8. filtrationThe solid was moved from the biphasic mixture by filtration
  9. washwashed with 60-80 petroleum ether
  10. customdried at oil-pump vacuum/40° C

出典と根拠

ORDレコード
ord-dd07a41a1d854c7c9cdf2e59c3f4cd80
出典データセット
uspto-grants-2001_05
特許番号
US06238855B1

反応ノート

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