Tributylvinyltin → Ethyl 2-vinylthiazole-5-carboxylate

HRID 70902

反応式

HRID 70902 の反応式
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[S:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:21]=1>O1CCOCC1.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>[CH:1]([C:17]1[S:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:21]=1)=[CH2:2]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

生成物 1

HCID 59607571Ethyl 2-vinylthiazole-5-carboxylate収率 89.8%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of tributyl(vinyl)stannane (0.92 mL, 3.14 mmol) and ethyl 2-bromothiazole-5-carboxylate (0.38 mL, 2.54 mmol) in dioxane (33 mL) is added Pd(PPh3)2Cl2 (182 mg, 0.26 mmol) at room temperature. After stirring at 100° C. under nitrogen for 4 hours, the solution is cooled to ambient temperature and then quenched with H2O. The crude is diluted with EtOAc, the organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained residue is purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=90:10 to 80:20) to give ethyl 2-vinylthiazole-5-carboxylate (418 mg). HPLC retention time=0.45 minutes (condition B); MS (m+1)=184.1; 1H NMR (400 MHz, CD3OD) δ ppm 1.37 (t, J=7.2 Hz, 3 H) 4.35 (q, J=7.1 Hz, 2 H) 5.71 (d, J=10.9 Hz, 1 H) 6.24 (d, J=17.4 Hz, 1 H) 6.93 (dd, J=17.4, 10.9 Hz, 1 H) 8.29 (s, 1 H)

後処理

  1. temperaturethe solution is cooled to ambient temperature
  2. customquenched with H2O
  3. additionThe crude is diluted with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue is purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=90:10 to 80:20)

出典と根拠

ORDレコード
ord-dbd8097989f9421896e1ccd214e01c2b
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

関連ノート

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