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

HRID 11990

반응식

HRID 11990 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-36825357a8654c3ebe21c8be8ba058ad
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727417B2

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