Benzaldehyde → Ethyl Cinnamate

HRID 475056

反応式

HRID 475056 の反応式
CC(C)([O-])C.[Li+].C(OP([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(OCC)=O)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[C:22]1(/[CH:21]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

生成物 1

HCID 637758Ethyl Cinnamate収率 72.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

To a stirred mixture of lithium tert-butoxide (124.6 g, 1.56 mol, 1.10 equiv) in DCM (2000 mL) under N2 at RT was added ethyl 2-(diethoxyphosphoryl)acetate (317 g, 1.41 mol, 1.00 equiv). Benzaldehyde (150 g, 1.41 mol, 1.0 equiv) was then added dropwise to the stirred reaction, and the resulting reaction mixture was stirred under N2 at 25° C. overnight. The reaction mixture was diluted with DCM (2 L). The organic layer was washed with water (3×2 L) and brine (1×2 L), dried (Na2SO4), filtered, and evaporated in vacuo. The crude residue was purified by SiO2 chromatograph eluting with EtOAc/petroleum ether (3.3 to 1% EtOAc) to afford 180 g (72%) of ethyl (2E)-3-phenylprop-2-enoate (31) as a light yellow oil.

後処理

  1. customthe resulting reaction mixture
  2. washThe organic layer was washed with water (3×2 L) and brine (1×2 L)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude residue was purified by SiO2 chromatograph
  7. washeluting with EtOAc/petroleum ether (3.3 to 1% EtOAc)

出典と根拠

ORDレコード
ord-2a24aa8a602940fea7000c23a6bea6f5
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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