2-Bromoethyl methyl ether → Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

HRID 588680ノート

反応式

HRID 588680 の反応式
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]([O:13][CH3:14])=[O:12])[CH2:8]2.C([N-]C(C)C)(C)C.[Li+].[CH3:23][O:24][CH2:25][CH2:26]Br>O1CCCC1>[CH3:23][O:24][CH2:25][CH2:26][C:2]1([C:11]([O:13][CH3:14])=[O:12])[CH:1]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]1[CH2:4]3)[CH2:8]2

参加物

5

反応物 3

HCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamideHCID 12600018Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate

生成物 1

HCID 89498778Methyl 2-(2-methoxyethyl)tricyclo[3.3.1.13,7]decane-2-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of EXAMPLE 56A (0.314 g) in tetrahydrofuran (5 mL) was added dropwise lithium diisopropylamide (1.401 mL) at −78° C. The reaction mixture was stirred for 60 minutes and 2-bromoethyl methyl ether (0.562 g) was added. The reaction mixture was slowly warmed up to room temperature, stirred at room temperature overnight, quenched with saturated aqueous NH4Cl solution (2 mL), and extracted with ether. The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes).

後処理

  1. stirringstirred at room temperature overnight
  2. customquenched with saturated aqueous NH4Cl solution (2 mL)
  3. extractionextracted with ether
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-635b0f160004413da94a3baf183a77fc
出典データセット
uspto-grants-2016_01
特許番号
US09227963B2

反応ノート

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