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

HRID 1613213ノート

反応式

HRID 1613213 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1795bd04d0134526b5af4b293c120b4a
出典データセット
uspto-grants-1993_03
特許番号
US05192776

反応ノート

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