Tributyltin Chloride → 4-Cyclopentyloxy-2-tributylstannanyl-pyridine

HRID 1898597ノート

反応式

HRID 1898597 の反応式
Br[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>C1COCC1>[CH:9]1([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 15096Tributyltin ChlorideHCID 457879742-Bromo-4-cyclopentyloxy-pyridineHCID 178461733HCID 178461733、化合物2 回

生成物 1

HCID 575166364-Cyclopentyloxy-2-tributylstannanyl-pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

In a round bottomed flask 2-bromo-4-cyclopentyloxy-pyridine (339 mg, 1.40 mmol) was dissolved in THF (6 mL). The solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 1.1 mL, 1.47 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 15 min then at room temperature for 2 h. An additional portion of isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 0.27 mL, 0.35 mmol) was added and stirring was continued at room temperature for 30 min. Tributyltin chloride (0.42 mL, 1.54 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated to give 4-cyclopentyloxy-2-tributylstannanyl-pyridine as a light brown oil which was used without further purification.

後処理

  1. waitat room temperature for 2 h
  2. stirringstirring
  3. waitwas continued at room temperature for 30 min
  4. stirringthe reaction mixture was stirred at room temperature for 2 h
  5. customThe reaction mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2b9fbe9f3d284f7987d42199a1f30ed5
出典データセット
uspto-grants-2013_08
特許番号
US08518945B2

反応ノート

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