Water → Tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate

HRID 1754286ノート

反応式

HRID 1754286 の反応式
[CH2:1]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2][CH:3]=[CH2:4].[Li]CCCC.Cl[CH2:19][C:20](=[O:41])[CH:21]=[P:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C1COCC1>[CH2:1]([N:5]([CH2:19][C:20](=[O:41])[CH:21]=[P:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2][CH:3]=[CH2:4]

参加物

6

反応物 4

HCID 962WaterHCID 2870041-Chloro-3-(triphenyl phosphoranylidene)propan-2-oneHCID 11263760Tert-butyl but-3-EN-1-ylcarbamateHCID 178418339Butyllithium

生成物 1

HCID 118222052Tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a mixture of tert-butyl N-but-3-enylcarbamate (3.16 g, 18.42 mmol, 1.30 Eq) in THF (20 mL), was added n-BuLi (2.5 M, 14.74 mL, 2.60 Eq) at −78° C. under N2. The mixture was stirred at −20° C. for 1 hr. Then 1-chloro-3-(triphenyl phosphoranylidene)propan-2-one (5.00 g, 14.17 mmol, 1.00 Eq) in THF (20 mL) was added to the mixture at −78° C. under N2. The mixture was stirred at −20° C. for 3 hr. The resulting mixture was poured into water (30 mL) and stirred for 20 min. The aqueous phase was extracted with EA (10 mL). The combined organic phase was washed with saturated brine (20 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=1/1) to afford tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate (5.80 g, 11.90 mmol, 83.98% yield) as yellow solid.

後処理

  1. stirringThe mixture was stirred at −20° C. for 3 hr
  2. stirringstirred for 20 min
  3. extractionThe aqueous phase was extracted with EA (10 mL)
  4. washThe combined organic phase was washed with saturated brine (20 mL*2)
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by silica gel chromatography (PE/EA=1/1)

出典と根拠

ORDレコード
ord-7081b272b45c46479051cfa962e3ab54
出典データセット
uspto-grants-2015_10
特許番号
US09169212B2

反応ノート

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