1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

HRID 1053964ノート

反応式

HRID 1053964 の反応式
CS(O[CH:6]1[CH2:11][CH2:10][S:9][CH2:8][CH:7]1[C:12]([O:14][CH3:15])=[O:13])(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[S:9]1[CH2:10][CH2:11][CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10377614Methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate

生成物 1

HCID 10351950Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate (4.33 g, 17.0 mmol) in DCM (170 mL) was added DBU (3.89 g, 25.5 mmol). The resulting mixture was refluxed at 50° C. for 30 minutes. The mixture was cooled to ambient temperature and washed with 1N aqueous HCl. The organic extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-45% EtOAc/hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 7.12-7.13 (m, 1H); 3.75 (s, 3H); 3.36 (q, J=2.2 Hz, 2H); 2.68 (t, J=5.8 Hz, 2H); 2.51-2.52 (m, 2H).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with 1N aqueous HCl
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by MPLC on silica gel (
  9. washa gradient elution of 0-45% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-e2b1eface1b9446091ccf96f4ec4bf9d
出典データセット
uspto-grants-2016_07
特許番号
US09394282B2

反応ノート

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