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

HRID 588680노트

반응식

HRID 588680 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-635b0f160004413da94a3baf183a77fc
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227963B2

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