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2-(Dimethylamino)ethanol → 4-(6-(Tributylstannyl)pyridin-2-yl)morpholine

HRID 1941960
ノート
印刷プレビュー

反応式

HRID 1941960 の反応式
CN(C)CCO.[Li]CCCC.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]>CCCCCC.O>[CH2:33]([Sn:28]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:29][CH2:30][CH2:31][CH3:32])[C:17]1[N:12]=[C:13]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH:14]=[CH:15][CH:16]=1)[CH2:34][CH2:35][CH3:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 79022-(Dimethylamino)ethanolHCID 15096Tributyltin ChlorideHCID 109648532-MorpholinopyridineHCID 178418339Butyllithium

生成物 1

HCID 185257394-(6-(Tributylstannyl)pyridin-2-yl)morpholine収率 7.3%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 8058Hexane溶媒2 回

反応条件

温度
2.5 °C

実験手順

To a solution of 2-dimethylaminoethanol (0.46 mL, 4.56 mmol) in hexane (7.0 mL, HPLC grade) cooled at −5° C. was added drop wise n-BuLi (1.60 M, 5.70 mL, 9.12 mmol) under nitrogen atmosphere. After 30 min at 0° C., 4-pyridin-2-yl-morpholine (0.25 g, 1.52 mmol) in hexane (2.0 mL) was added drop wise. After stirring the reaction mixture for 1 h at 0-5° C., the reaction medium was cooled to −78° C. followed by drop wise addition of tributyl tin chloride (1.03 mL, 3.70 mmol). The resulting reaction mixture was stirred at −78° C. for 30 min and then allowed to stir at 0-5° C. for 2 h. The reaction mixture was then allowed to come to room temperature. After the completion of reaction (TLC monitoring), the reaction mass was cooled to 0° C. and water was added slowly. The aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness. The crude residue was purified over silica gel (230-400 M) using EtOAc-Hexane (2:98) to provide the compound as yellow oil (0.050 g, 7.20%).

後処理

  1. temperaturethe reaction medium was cooled to −78° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at −78° C. for 30 min
  4. stirringto stir at 0-5° C. for 2 h
  5. customto come to room temperature
  6. customAfter the completion of reaction (TLC monitoring)
  7. temperaturethe reaction mass was cooled to 0° C.
  8. extractionThe aqueous phase was extracted with diethyl ether (3×20 mL)
  9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  10. customevaporated to dryness
  11. customThe crude residue was purified over silica gel (230-400 M)

出典と根拠

ORDレコード
ord-0258ce6bf03049ed80189da4ee0053a2
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389516B2

反応ノート

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