Pyridine → 6-Cyano-1-acetoxyhexane

HRID 965131Notes

Reaction equation

HRID 965131 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])#[N:2].N1C=CC=CC=1.[CH3:16][CH2:17][O:18]CC>C(OC(=O)C)(=O)C>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:17](=[O:18])[CH3:16])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 873856-Cyano-1-hexanol

Product 1

HCID 193675096-Cyano-1-acetoxyhexane

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

6-Cyano-1-hexanol (7.1 g, 55.8 mmol) was dissolved in 30 mL of acetic anhydride under argon atmosphere. To this material was added 5.3 mL (65.4 mmol) of pyridine dropwise and the mixture was left to stir for 2 hours. The contents of the flask were then poured into a beaker containing 50 mL of ice water and the material was stirred for 15 minutes. The mixture was transferred to a 250 mL separatory funnel and ether (100 mL) was added. After shaking the ether phase was isolated and the aqueous phase washed twice more with ether (2×100 mL). The combined ether phase was washed with brine, dried (MgSO4) and filtered. Evaporation (rotary evaporator and vacuum pump) provided 6-cyano-1-acetoxyhexane (the compound of formula (C)) which was used immediately in the next step.

Workup

  1. waitthe mixture was left
  2. additionThe contents of the flask were then poured into a beaker
  3. stirringthe material was stirred for 15 minutes
  4. customThe mixture was transferred to a 250 mL separatory funnel
  5. customwas isolated
  6. washthe aqueous phase washed twice more with ether (2×100 mL)
  7. washThe combined ether phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customEvaporation (rotary evaporator and vacuum pump)

Sources & evidence

ORD record
ord-4bd32306023b4d47b4976643a872ad7a
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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