N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide → HCID 89527308, 화합물

HRID 1778565노트

반응식

HRID 1778565 반응식
CON(C)[C:4]([CH:6]1[CH2:9][C:8]([O:12][CH3:13])([O:10][CH3:11])[CH2:7]1)=[O:5].[CH2:15]([Mg]Br)[CH2:16][CH:17]=[CH2:18]>C1COCC1>[CH3:13][O:12][C:8]1([O:10][CH3:11])[CH2:7][CH:6]([C:4](=[O:5])[CH2:18][CH2:17][CH:16]=[CH2:15])[CH2:9]1

참가 물질

4

반응물 2

HCID 86624599N,3,3-Trimethoxy-N-methylcyclobutanecarboxamideHCID 178418797HCID 178418797, 화합물

생성물 1

HCID 89527308HCID 89527308, 화합물수율 92.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

N,3,3-trimethoxy-N-methylcyclobutanecarboxamide (12.19 g, 60.0 mmol) was dissolved in THF (130 mL), cooled to 0° C. and treated with 3-butenylmagnesium bromide (168 mL, 0.5 M/THF, 84 mmol). After stirring for 1.5 h at room temperature, the reaction was re-cooled to 0° C. and quenched with 1 N citric acid (30 mL), diluted with ethyl acetate, washed successively with water, saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5-40% ethyl acetate in heptane to afford the desired product 10.98 g (92%). Rf 0.77 (50% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 5.87-5.72 (m, 1H), 5.06-4.95 (m, 2H), 3.17 (s, 3H), 3.13 (s, 3H), 3.06-2.88 (m, 1H), 2.54-2.48 (m, 2H), 2.38-2.28 (m, 6H).

후처리

  1. temperaturethe reaction was re-cooled to 0° C.
  2. customquenched with 1 N citric acid (30 mL)
  3. additiondiluted with ethyl acetate
  4. washwashed successively with water, saturated aqueous sodium chloride
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 5-40% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-6c7c5e41cae946c687731d94d7ff0043
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266908B2

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