Lithium Chloride → Ethyl (1-vinylcyclopropyl)acetate

HRID 1920572

반응식

HRID 1920572 반응식
[Cl-].[Li+].[CH:3]([Mg]Cl)=[CH2:4].[C:7]1(=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:8]1>C1COCC1.[Cu]Cl>[CH:3]([C:7]1([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:8]1)=[CH2:4]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 11040705Ethyl cyclopropylideneacetateHCID 178461836HCID 178461836, 화합물

생성물 1

HCID 57965754Ethyl (1-vinylcyclopropyl)acetate

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Under argon, 0.55 g (5.53 mmol) of copper(I) chloride and 0.59 g (13.82 mmol) of lithium chloride are suspended in 150 ml of anhydrous THF. The reaction mixture is cooled to −78° C., 48.8 ml (82.95 mmol) of vinylmagnesium chloride solution (1.7 M in THF) are added and the mixture is stirred for 10 minutes. Over a period of 30 min, a solution of 8.72 g (69.12 mmol) of ethyl cyclopropylideneacetate (Example 1A) in 50 ml of anhydrous THF is then added dropwise. After the addition is ended, the cooling bath is replaced by an ice/acetone bath. After a further 15 min, the reaction is terminated by dropwise addition of 100 ml of 1 N hydrochloric acid. The reaction mixture is saturated with sodium chloride, and 100 ml of a saturated sodium chloride solution which contains 5 ml of a 25% strength aqueous ammonia solution are then added. The mixture is filtered through Celite. The filtrate is washed with ammoniacal sodium chloride solution until the aqueous phase remains colorless. The organic phase is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent and kugelrohr distillation of the residue at 150° C. and 15 mbar gives 7.10 g (67% of theory) of the title compound as a colorless liquid.

후처리

  1. waitOver a period of 30 min
  2. additionAfter the addition
  3. customthe cooling bath is replaced by an ice/acetone bath
  4. waitAfter a further 15 min
  5. customthe reaction is terminated by dropwise addition of 100 ml of 1 N hydrochloric acid
  6. additionare then added
  7. filtrationThe mixture is filtered through Celite
  8. washThe filtrate is washed with ammoniacal sodium chloride solution until the aqueous phase
  9. washThe organic phase is washed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customRemoval of the solvent and kugelrohr distillation of the residue at 150° C.

출처 및 근거

ORD 기록
ord-936a9b1f9b304f80b2d3cb84f193b2f6
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168821B2

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