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

HRID 10180

Reaction equation

HRID 10180 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-42201cf9f09346ee95bb09f0fe591bf4
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Linked notes

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