Iodoethane → HCID 10036828、化合物

HRID 1167271ノート

反応式

HRID 1167271 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 10036828HCID 10036828、化合物収率 33.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-484ba7ebdfb343dd99a7b8afe20e6879
出典データセット
uspto-grants-2003_09
特許番号
US06617350B2

反応ノート

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