Iodine → N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide

HRID 1778598ノート

反応式

HRID 1778598 の反応式
[Mg].II.Br[CH2:5][CH2:6][CH:7]=[CH2:8].[Cl:9][C:10]1[CH:29]=[CH:28][C:13]([CH2:14][C:15]2([NH:25][CH:26]=[O:27])[CH2:18][CH:17]([C:19](N(OC)C)=[O:20])[CH2:16]2)=[CH:12][CH:11]=1>C1COCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C:15]2([NH:25][CH:26]=[O:27])[CH2:16][CH:17]([C:19](=[O:20])[CH2:8][CH2:7][CH:6]=[CH2:5])[CH2:18]2)=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 807IodineHCID 21241Homoallyl bromideHCID 5462224Magnesium2 回HCID 895144553-(4-chlorobenzyl)-3-formamido-N-methoxy-N-methylcyclobutanecarboxamide

生成物 1

HCID 89514331N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide収率 97.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

Magnesium powder (0.548 g, 22.6 mmol) was placed into a round-bottomed flask with a small piece of iodine. Dry THF was added to cover the magnesium and the solution was heated to a gentle reflux until the color had dissipated (approximately 30 minutes). While refluxing, a second solution of 4-bromo-1-buten (2.3 mL, 22.6 mmol) in dry THF (5 mL) was added. After 12 min, the mixture was cooled 0° C. and added to a solution of 3-(4-chlorobenzyl)-3-formamido-N-methoxy-N-methylcyclobutanecarboxamide (0.5 g, 1.61 mmol) in dry THF (30 mL). After 2 h, the reaction was allowed to warm to room temperature and stir overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with diethyl ether (×2). The combined organic layers were washed successively with 1M HCl, water and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated to give the crude product (0.48 g) that was used to the next step without further purification. ESI MS found for C17H20ClNO2 m/z [306.3 (M+1), 328.3 (M+Na+), 304.5 (M−1)].

後処理

  1. temperaturethe solution was heated to
  2. temperaturea gentle reflux until the color
  3. custom(approximately 30 minutes)
  4. temperatureWhile refluxing
  5. waitAfter 2 h
  6. temperatureto warm to room temperature
  7. customThe reaction was quenched with saturated aqueous NH4Cl
  8. extractionextracted with diethyl ether (×2)
  9. washThe combined organic layers were washed successively with 1M HCl, water and saturated aqueous sodium chloride
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-80f6fce1b8ff450ebe4c2100ca17afb6
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

読み込み中…