Carbon Tetrachloride → HCID 86674593, 화합물

HRID 2170705노트

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HRID 2170705 반응식
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:2]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>CCOC(C)=O>[Br:22][CH2:14][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[O:7][C@@H:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10]

참가 물질

6

반응물 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 51924568HCID 51924568, 화합물

생성물 1

HCID 86674593HCID 86674593, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a 250 mL round-bottom flask was (S)-methyl 2-(m-tolyloxy)propanoate (2.0 g, 10.3 mmol, 1 equiv), NBS (1.83 g, 10.3 mmol, 1 equiv), AIBN (169 mg, 1.03 mmol, 0.1 equiv) and CCl4 (100 mL). The reaction mixture was refluxed for 16 h at 80° C. The completion of the reaction was monitored by analytical HPLC. The reaction mixture was allowed to cool to room temperature. The crude mixture was dissolved in AcOEt (100 mL) and washed with a 0.5N HCl aqueous solution (×2), a saturated NaHCO3 solution (×2) and brine, dried over Na2SO4. The filtrate was concentrated to obtain the crude product which was purified by flash chromatography (AcOEt/Hexane 0->60%) to obtain the title compound.

후처리

  1. customTo a 250 mL round-bottom flask was
  2. temperatureto cool to room temperature
  3. washwashed with a 0.5N HCl aqueous solution (×2)
  4. dry with materiala saturated NaHCO3 solution (×2) and brine, dried over Na2SO4
  5. concentrationThe filtrate was concentrated
  6. customto obtain the crude product which
  7. customwas purified by flash chromatography (AcOEt/Hexane 0->60%)

출처 및 근거

ORD 기록
ord-ce6db416fa9b42e2b097072a486f4daa
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051265B2

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