1-Iodonaphthalene → 1-[2-(Benzenesulfonyl)ethenyl]naphthalene

HRID 1532458

반응식

HRID 1532458 반응식
[C:1]1([S:7]([CH2:10][CH2:11]O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C.I[C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:1]1([S:7]([CH:10]=[CH:11][C:38]2[C:39]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:35]=[CH:36][CH:37]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 5

HCID 70041-IodonaphthaleneHCID 8471TriethylamineHCID 302022-(Phenylsulfonyl)ethanolHCID 80271Tri-o-tolylphosphineHCID 81560Methanesulfonic anhydride

생성물 1

HCID 702224971-[2-(Benzenesulfonyl)ethenyl]naphthalene수율 66%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

To 0.186 g (1.0 mmol) of 2-(phenylsulfonyl)ethanol, 3 ml of acetonitrile was added, followed by 0.19 g (1.1 mmol) of methanesulfonic anhydride and 0.56 ml (4.0 mmol) of triethylamine, and the mixture was stirred for 5 hours at an internal temperature of 50° C. Subsequently, 0.22 ml (1.5 mmol) of 1-iodonaphthalene, 0.11 g (0.05 mmol) of palladium acetate, and 0.067 g (0.22 mmol) of tri(o-tolyl)phosphine were added thereto, and the mixture was then refluxed for 17 hours. After cooled to room temperature, the reaction mixture was concentrated and purified by column chromatography (hexane/ethyl acetate=80/20) to obtain 0.194 g of [2-(phenylsulfonyl)ethenyl]naphthalene. Yield: 66%.

후처리

  1. temperaturethe mixture was then refluxed for 17 hours
  2. temperatureAfter cooled to room temperature
  3. concentrationthe reaction mixture was concentrated
  4. custompurified by column chromatography (hexane/ethyl acetate=80/20)

출처 및 근거

ORD 기록
ord-1b2a7b12718245e689cb4fa35de28d90
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201131B1

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