Iodoethane → HCID 10036828, 화합물

HRID 1167271노트

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HRID 1167271 반응식
[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].[CH2:9]([O:11][C:12](=[O:22])[CH2:13][CH2:14][CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)[CH3:10].C(I)C>O1CCCC1>[CH2:1]([CH:13]([CH2:14][CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)[C:12]([O:11][CH2:9][CH3:10])=[O:22])[CH3:2]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 11229436Ethyl 4-(2-methyl-1,3-dioxolan-2-yl)butanoate

생성물 1

HCID 10036828HCID 10036828, 화합물수율 33.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a freshly prepared solution of lithium diisopropylamide (40.0 mmol in tetrahydrofuran/hexane; 50 mL, 1:1) at −78° C. was added a solution of ethyl-4-(2-methyl-1,3-dioxolan-2-yl)butanoate (6.7 g, 33.3 mmol) in tetrahydrofuran (15 mL) over 15 minutes. After stirring for 15 minutes, ethyl iodide (4.0 mL, 50.0 mmol) was added rapidly via syringe. The reaction was stirred at −78° C. for 6 hours and then allowed to warm slowly to ambient temperature and stir for 16 hours. The reaction was quenched by the addition of water (50 mL) and extracted with ether (3×50 mL). The combined organics were washed with brine (50 mL), dried (magnesium sulfate), concentrated in vacuo and chromatographed (silica gel, ethyl acetate/hexane, 1:4) to afford ethyl 2-ethyl-4-(2-methyl-1,3-dioxolan-2-yl)butanoate (2.6 g, 33%) as a colorless liquid.

후처리

  1. stirringThe reaction was stirred at −78° C. for 6 hours
  2. stirringstir for 16 hours
  3. customThe reaction was quenched by the addition of water (50 mL)
  4. extractionextracted with ether (3×50 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customchromatographed (silica gel, ethyl acetate/hexane, 1:4)

출처 및 근거

ORD 기록
ord-484ba7ebdfb343dd99a7b8afe20e6879
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617350B2

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