Sodium hydride → Ethyl trans-2-phenylcyclopropanecarboxylate

HRID 475057

反応式

HRID 475057 の反応式
[H-].[Na+].[I-].C[S+](C)(C)=O.[C:9]1(/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:22]S(C)=O.C1COCC1>CS(C)=O>[CH2:20]([O:19][C:17]([C@@H:16]1[CH2:22][C@H:15]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:18])[CH3:21]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 637758Ethyl CinnamateHCID 21830753dimethylsulfoxide THF

生成物 1

HCID 252496Ethyl trans-2-phenylcyclopropanecarboxylate収率 79%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
25 °C

実験手順

To a stirred mixture of NaH (40.7 g) in DMSO (2.5 L) under N2 was added portion wise trimethyl sulfoxonium iodide (396 g, 1.80 mol, 1.76 equiv). A solution of 31 (180 g, 1.02 mol, 1.00 equiv) in 1:1 DMSO/THF (2 L) was added, and the reaction mixture was stirred at 25° C. overnight. The reaction mixture was quenched with 1N HCl (1 L) and extracted with EtOAc (2×2 L). The combined organic layers were washed with water (2×2 L) and brine (1×2 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (5 to 12.5% EtOAc) to afford 153 g (79%) of trans-ethyl-2-phenylcyclopropane-1-carboxylate (33) as a light yellow oil.

後処理

  1. customThe reaction mixture was quenched with 1N HCl (1 L)
  2. extractionextracted with EtOAc (2×2 L)
  3. washThe combined organic layers were washed with water (2×2 L) and brine (1×2 L)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with EtOAc/petroleum ether (5 to 12.5% EtOAc)

出典と根拠

ORDレコード
ord-7c5defb9202a4a73920355d3fd2b1232
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

関連ノート

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