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

HRID 900647Notes

Reaction equation

HRID 900647 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 84.5%

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 g).

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-4b9353a0b927442da24d9b0e6af86e74
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Reaction notes

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