Benzene, 1-chloro-4-ethynyl- → HCID 71255724、化合物

HRID 2202148ノート

反応式

HRID 2202148 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[O:19]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate2 回HCID 178418339Butyllithium

生成物 1

HCID 71255724HCID 71255724、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1-chloro-4-ethynylbenzene (2.76 g, 20.20 mmol) in THF (50 mL) at −78° C. was added 2.5 M butyllitium (8.81 ml, 22.03 mmol in hexane) and stirred for 1 h at −78° C. tert-Butyl 4-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (Compound 1.2, 5 g, 18.36 mmol) was added. The mixture was stirred at −78° C. for 30 min, then warmed up to 0° C., stirred for another hour at the same temperature, and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated. The residue was purified by silica gel column chromatography using gradient elution (5 to 30%, EtOAc/hexane). LC-MS m/z 292.06 [M−56+H]+.

後処理

  1. additionwas added
  2. temperaturewarmed up to 0° C.
  3. stirringstirred for another hour at the same temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationthe drying agent was filtered off
  8. concentrationThe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography
  10. washelution (5 to 30%, EtOAc/hexane)

出典と根拠

ORDレコード
ord-48e75d6d8e704b53aeabf7cef64777ea
出典データセット
uspto-grants-2016_06
特許番号
US09365539B2

反応ノート

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