Acetonitrile → HCID 21249279, compound

HRID 1194692Notes

Reaction equation

HRID 1194692 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].C(#N)C.Br[CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]>O>[CH2:25]([N:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH2:24][CH2:23][CH:22]=[CH2:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 707041-Pentene, 5-bromo-

Product 1

HCID 21249279HCID 21249279, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 15 g (0.105 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 15.93 g (0.115 mol) of K2CO3, and 100 ml of acetonitrile is added dropwise 14.41 ml (0.105 mol) of 5-bromopentene. The mixture is stirred overnight at room temperature and then at 65° C. for 2 hours. After cooling, the mixture is diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to furnish 18.62 g (84%) of title compound as an oil: IR (neat) 2940 and 1090 cm-1 ; NMR (CDCl3) δ5.84 (m, 1H), 5.02 (m, 2H), 3.96 (s, 4H), 2.70-1.40 (m, 14H).

Workup

  1. waitat 65° C. for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-292ba302cd30447a8682ee085edc28e1
Source dataset
uspto-grants-1989_03
Patent number
US04816464

Reaction notes

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