Chloroiodomethane → (S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone

HRID 1523549

반응식

HRID 1523549 반응식
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([C:7]([O:9]C)=O)[CH2:4][O:3]1.[Cl:12][CH2:13]I.[Li+].CC([N-]C(C)C)C.[OH-].[Na+]>C1COCC1.CCOC(C)=O.C(O)(=O)C>[Cl:12][CH2:13][C:7]([C@@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:11])[O:6]1)=[O:9]

참가 물질

8

반응물 4

HCID 11644ChloroiodomethaneHCID 14798Sodium HydroxideHCID 853165Methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylateHCID 2724682Lithium diisopropylamide

생성물 1

HCID 86644148(S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone수율 42%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

To a solution of (S)-methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate (1.3 g, 8.1 mmol) and chloroiodomethane (4.3 g, 24 mmol) in THF (50 mL) at −78° C. was added a solution of LDA (16.2 mL, 24 mmol) in portions over 10 minutes. The reaction was stirred at −78° C. for 10 minutes. To this mixture was added a 10% solution of acetic acid (50 mL) in THF at −78° C. After addition, the slurry was warmed to ambient temperature. The reaction was poured into EtOAc (200 mL) and the aqueous layer basified using 1N NaOH. The organics were separated and washed with brine, dried over MgSO4 and concentrated in vacuo. The material was purified by chromatography using DCM as eluent to give (S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone (0.60 g, 3.4 mmol, 42% yield) as an oil.

후처리

  1. additionAfter addition
  2. temperaturethe slurry was warmed to ambient temperature
  3. customThe organics were separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe material was purified by chromatography

출처 및 근거

ORD 기록
ord-31947033ea6a43b1869f04a67173fcd1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079890B2

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