N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide → HCID 89527308、化合物

HRID 1778565ノート

反応式

HRID 1778565 の反応式
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

参加物

4

反応物 2

HCID 86624599N,3,3-Trimethoxy-N-methylcyclobutanecarboxamideHCID 178418797HCID 178418797、化合物

生成物 1

HCID 89527308HCID 89527308、化合物収率 92.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c7c5e41cae946c687731d94d7ff0043
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

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