1-Pent-4-enyl-azocan-2-one → 4-(2-Oxo-azocan-1-yl)-butyraldehyde

HRID 10180

반응식

HRID 10180 반응식
[CH2:1]([N:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:14])[CH2:2][CH2:3][CH:4]=C.I([O-])(=O)(=O)=[O:16].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[O:14]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:6]1[CH2:1][CH2:2][CH2:3][CH:4]=[O:16]

참가 물질

6

반응물 2

HCID 219785471-Pent-4-enyl-azocan-2-oneHCID 23667635Sodium periodate

생성물 1

HCID 219785824-(2-Oxo-azocan-1-yl)-butyraldehyde수율 0%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Osmium tetroxide (17 mg, 0.07 mmole) was added to 1-pent-4-enyl-azocan-2-one (5.52 g, 28.3 mmole) in a mixture of tetrahydrofuran (100 mL) and water (50 mL) under ambient water bath cooling. The mixture was stirred for 5 minutes and solid sodium periodate (15.11 g, 70.65 mmole) was added in portions over 15 minutes. The reaction mixture was stirred for 3 hours and filtered. The filtrate was concentrated, saturated with solid sodium chloride, and extracted with methylene chloride. The organic phase was dried (magnesium sulfate) and concentrated. Purification by silica gel chromatography, eluting with chloroform, gave 4-(2-oxo-azocan-1-yl)-butyraldehyde (4.72 μg).

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated, saturated with solid sodium chloride
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography
  9. washeluting with chloroform

출처 및 근거

ORD 기록
ord-42201cf9f09346ee95bb09f0fe591bf4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094778B2

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