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Sodium Hydroxide → ethyl(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate

HRID 1611062
ノート
印刷プレビュー

反応式

HRID 1611062 の反応式
[CH2:1]1OCCOCCOCCOCCO[CH2:2]1.[OH-].[Na+].C([C:20]([CH2:33][CH3:34])(P(O)(O)=O)/[C:21](/[CH3:28])=[C:22](\CC)/[C:23]([O-:25])=[O:24])C.[CH3:35][C:36](=[CH:38][CH2:39][CH2:40]/[C:41](=C/C=O)/[CH3:42])[CH3:37]>C1(C)C=CC=CC=1>[CH3:28]/[C:21](/[CH:20]=[CH:33]/[CH:34]=[C:41](\[CH3:42])/[CH2:40][CH2:39][CH:38]=[C:36]([CH3:37])[CH3:35])=[CH:22]\[C:23]([O:25][CH2:1][CH3:2])=[O:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 3633615-Crown-5HCID 638011CitralHCID 86584517Triethyl-3-methyl-4-phosphonocrotonate

生成物 1

HCID 6370567ethyl(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate収率 876.6%

試薬・触媒・溶媒 1

HCID 1140Toluene
溶媒
2 回

反応条件

温度
0 °C

実験手順

15-crown-5 (0.9 g, 0.1 equivalents, 4.0 mmol) was dissolved in 50 ml of toluene at room temperature, and added with 32 ml of 50% aqueous sodium hydroxide solution. To the solution, triethyl-3-methyl-4-phosphonocrotonate (11.1 g, 1.05 equivalents, 42 mmol) and then 7 ml toluene solution of geranial (6.1 g, 40 mmol) were added under stirring at 0° C. The mixture was stirred at room temperature for 1.5 hours. The organic and aqueous layers were separated, and the organic layer was washed with saturated ammonium chloride solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 9.2 g of the title compound (yield 87%, 2E:2Z=93:7) as a yellow oil.

後処理

  1. stirringThe mixture was stirred at room temperature for 1.5 hours
  2. customThe organic and aqueous layers were separated
  3. washthe organic layer was washed with saturated ammonium chloride solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-98e6691ebbb24afc9643ea9b2839a1a7
出典データセット
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06984742B2

反応ノート

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