Acetic Acid → 2-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane

HRID 1087641노트

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HRID 1087641 반응식
[CH2:1]([P:5]1(=[O:11])[O:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]([CH3:4])=[O:3].[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[C:1]([P:5]1(=[O:11])[O:6][CH2:7][CH2:8][CH2:9][O:10]1)[C:2]([CH3:4])=[O:3])([O-:14])=[O:13]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 136045512-Acetonyl-2-oxo-1,3,2-dioxaphosphorinane

생성물 1

HCID 540679512-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane수율 25.8%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of 10.0 grams of 2-acetonyl-2-oxo-1,3,2-dioxaphosphorinane and 8.48 grams of m-nitrobenzaldehyde was dissolved in 120 ml of toluene, 1.0 gram of piperidine and 2.0 grams of acetic acid were added as catalysts and the mixture was heated to reflux for 15 hours with a water-remover. After cooled, the crystals separated out were removed by filtration, the filtrate was washed with water, then with aqueous solution of sodium hydroxide, further with 20% sodium acid sulfite solution and finally with water, and the organic solvent layer was dried. The solvent was removed by evaporation in vacuo, the residue was purified by silica gel column chromatography, and 4.5 grams of 2-(1-(3-nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane was obtained as an EZ mixture. Recrystallized from ethyl acetate. M.p. 144°-145.5° C.

후처리

  1. temperaturethe mixture was heated
  2. temperatureAfter cooled
  3. customthe crystals separated out
  4. customwere removed by filtration
  5. washthe filtrate was washed with water
  6. dry with materialwith aqueous solution of sodium hydroxide, further with 20% sodium acid sulfite solution and finally with water, and the organic solvent layer was dried
  7. customThe solvent was removed by evaporation in vacuo
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-73e9e039c9eb477cbf1902f78999a98f
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036059

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