Hydrochloric Acid → 3,3'-Bis(diethoxyphosphoryl)-[2,2']-bithiophene

HRID 1662881ノート

反応式

HRID 1662881 の反応式
[CH2:1]([O:3][P:4]([C:9]1[CH:13]=[CH:12][S:11][C:10]=1I)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:20]1[S:21][CH:22]=[CH:23][C:24]=1[P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])CCC.Cl>CN(C=O)C.[Cu]Cl>[CH2:1]([O:3][P:4]([C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:20]1[S:21][CH:22]=[CH:23][C:24]=1[P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 59155833HCID 59155833、化合物HCID 591558362-Iodo-3-diethoxyphosphorylthiophene

生成物 1

HCID 866384143,3'-Bis(diethoxyphosphoryl)-[2,2']-bithiophene収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 62652Cuprous chloride溶媒

反応条件

温度
80 °C

実験手順

At room temperature, 0.6790 g (1.96 mmols) of the 3-(diethoxyphosphoryl)-2-iodothiophene obtained in Example 12(1) and 0.9982 g (1.96 mmols) of the 2-(tributylstannyl)-3-(diethoxyphosphoryl)thiophene obtained in Example 12(2) were dissolved in DMF, to which 0.2326 g (2.35 mmols) of commercially available copper(I) chloride was added at room temperature. Thereafter, the reaction mixture was heated to 80° C. and stirred for 10 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a 10% hydrochloric acid aqueous solution, followed by extraction of the resulting product with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a silica gel column (gradiated from ethyl acetate:hexane=1:1 with acetone) to obtain the specified substance in the form of white crystals at a yield of 0.6101 g (yield: 71%).

後処理

  1. additionwas added at room temperature
  2. customAfter the reaction
  3. extractionfollowed by extraction of the resulting product with ethyl acetate
  4. washThe organic phase was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distilling off under reduced pressure
  8. customthe resulting crude product was purified with a silica gel column (gradiated from ethyl acetate:hexane=1:1 with acetone)
  9. customto obtain the specified substance in the form of white crystals at a yield of 0.6101 g (yield: 71%)

出典と根拠

ORDレコード
ord-71582fc1bd6a4b4aaac1ff2b4eb1c85c
出典データセット
uspto-grants-2011_10
特許番号
US08030438B2

反応ノート

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