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Isopropenyl chloroformate → Prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate

HRID 626528
ノート
印刷プレビュー

反応式

HRID 626528 の反応式
[CH3:1][C:2]1([C:5]([NH2:7])=[O:6])[CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:19]([O:21][C:22]([CH3:24])=[CH2:23])=[O:20]>C1COCC1>[CH3:1][C:2]1([C:5]([NH:7][C:19](=[O:20])[O:21][C:22]([CH3:24])=[CH2:23])=[O:6])[CH2:4][CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 93846Isopropenyl chloroformateHCID 2733832Lithium hexamethyldisilazaneHCID 130029361-Methylcyclopropanecarboxamide

生成物 1

HCID 90445232Prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate収率 116.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A −78° C. solution of 1-methylcyclopropanecarboxamide (1.35 g, 13.6 mmol) in THF (30 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M THF, 17.7 mL, 17.7 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (1.94 mL, 17.7 mmol) in THF (5 mL), stirred at −78° C. for 1 h, then allowed to warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate (2.9 g, 116%) which was used without further purification.

後処理

  1. stirringstirred at −78° C. for 1 h
  2. stirringstirred for 1 h
  3. customThe mixture was quenched with satd
  4. extractionNaHCO3, extracted with EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-ae07e366a20940a480538650fb52fbb7
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309224B2

反応ノート

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