1-Heptyne → 1-Chloro-6-(1-pentynyl)-2-naphthol

HRID 11990

反応式

HRID 11990 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:13].[CH:14]#[C:15][CH2:16][CH2:17][CH2:18]CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]#[C:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:13]

参加物

6

反応物 2

HCID 123501-HeptyneHCID 220481596-Bromo-1-chloronaphthalen-2-ol

生成物 1

HCID 673574061-Chloro-6-(1-pentynyl)-2-naphthol収率 88.7%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

The synthesis of (S7-3) was carried out following the method described in Synthesis, No. 9, 1439 (2004). At first, 38.3 g of 1-chloro-6-bromo-2-naphthol (S1-2), 5.2 g of PdCl2(PPh3)2, 0.71 g of copper iodide and 400 ml of triethylamine were added to a reactor in nitrogen atmosphere, stirred at room temperature, added with 35.8 g of 1-heptyne (S7-2) and then refluxed for 6 hours. The reaction solution was cooled to room temperature and distilled under a reduced pressure to remove the solvent, and then the residue was added with ethyl acetate and filtered by celite. The resulting solution was washed with 1N HCl(aq) and water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under a reduced pressure. The residue was purified by silica gel column chromatography using heptane/ethyl acetate=3/1 as an eluting solvent and dried under a reduced pressure to obtain 32.3 g of 1-chloro-6-(1-pentynyl)-2-naphthol (S7-3).

後処理

  1. customThe synthesis of (S7-3)
  2. customdescribed in Synthesis
  3. temperaturerefluxed for 6 hours
  4. temperatureThe reaction solution was cooled to room temperature
  5. distillationdistilled under a reduced pressure
  6. customto remove the solvent
  7. additionthe residue was added with ethyl acetate
  8. filtrationfiltered by celite
  9. washThe resulting solution was washed with 1N HCl(aq) and water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under a reduced pressure
  12. customThe residue was purified by silica gel column chromatography
  13. customdried under a reduced pressure

出典と根拠

ORDレコード
ord-36825357a8654c3ebe21c8be8ba058ad
出典データセット
uspto-grants-2010_06
特許番号
US07727417B2

関連ノート

読み込み中…