Formic Acid → 1-Formyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 1613213노트

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HRID 1613213 반응식
[CH:1](O)=[O:2].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[F:28][C:29]1[C:41]([F:42])=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:30]=1[O:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(=O)(O)[O-].[Na+]>C(OCC)C.O>[CH:1]([N:35]1[CH2:36][CH2:37][CH:32]([O:31][C:30]2[C:38]([F:45])=[C:39]([F:44])[C:40]([F:43])=[C:41]([F:42])[C:29]=2[F:28])[CH2:33][CH2:34]1)=[O:2]

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 516892Sodium BicarbonateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

생성물 1

HCID 197624641-Formyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
55 °C

실험 절차

A mixture of 1.5 ml of formic acid and 3.5 ml of acetic anydride was stirred at 55° C. for one hour, cooled, and treated with a solution of 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine in 50 ml of diethyl ether. The reaction mixture was then stirred at ambient temperature for three hours. Thereafter, the mixture was poured into 100 ml of water, adjusted to pH 10 by the addition of sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. Filtration, followed by evaporation of the solvent afforded an oil which was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to yield 4.0 g (91%) of 1-formyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 32°-34° C.

후처리

  1. temperaturecooled
  2. stirringThe reaction mixture was then stirred at ambient temperature for three hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent
  8. customafforded an oil which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)

출처 및 근거

ORD 기록
ord-1795bd04d0134526b5af4b293c120b4a
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05192776

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