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

HRID 1611062
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HRID 1611062 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene
용매
2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98e6691ebbb24afc9643ea9b2839a1a7
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06984742B2

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