Benzyl chloroformate → Benzyl but-3-en-1-ylcarbamate

HRID 595228ノート

反応式

HRID 595228 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([NH2:16])[CH2:13][CH:14]=[CH2:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:12]([NH:16][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:13][CH:14]=[CH2:15]

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 4437323-Buten-1-amineHCID 516892Sodium Bicarbonate

生成物 1

HCID 14688338Benzyl but-3-en-1-ylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Benzyl chloroformate (38 g, 0.22 mol) was added at 0° C. over 15 minutes to a mixture of but-3-en-1-amine (10 g, 0.14 mol) and sodium bicarbonate (35 g, 0.52 mol) in DCM (500 mL) and water (40 mL). The mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford benzyl but-3-en-1-ylcarbamate. MS ESI calc'd. for C12H16NO2 [M+H]+ 206. found 206. 1H NMR (400 MHz, CDCl3) δ 7.36-7.30 (m, 5H), 5.80-5.70 (m, 1H), 5.11-5.01 (m, 4H), 3.79-3.25 (m, 2H), 2.29-2.24 (m, 2H).

後処理

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

出典と根拠

ORDレコード
ord-5042bb1e9a8e480c97a726d774621ea3
出典データセット
uspto-grants-2016_01
特許番号
US09242984B2

反応ノート

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