Valeronitrile → HCID 58380857, compound

HRID 1948155Notes

Reaction equation

HRID 1948155 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[C:9](#[N:14])[CH2:10][CH2:11][CH2:12][CH3:13].Cl/[CH:16]=C\CCCl>C1COCC1>[C:9]([C:10]1([CH2:8][CH2:6][CH3:7])[CH2:16][CH:13]=[CH:12][CH2:11]1)#[N:14]

Participants

5

Reactant 3

HCID 8061ValeronitrileHCID 2724682Lithium diisopropylamideHCID 86614758HCID 86614758, compound

Product 1

HCID 58380857HCID 58380857, compoundYield 145.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LDA (276 mL, 553 mmol 2M in THF) was added dropwise at −78° C. under argon to a stirred solution of valeronitrile (20 g, 25.3 mL, 241 mmol) in THF (250 mL) and then stirred for 15 minutes. The reaction mixture was then warmed to room temperature and stirred for a further 20 minutes. After cooling to −78° C., cis-1,4-dichlorobutene (30.1 g, 25.3 mL) was added dropwise over 10 minutes and the mixture stirred for 10 minutes. The mixture was allowed to warm to room temperature and was then stirred overnight. The reaction was quenched by gentle addition to 150 mL ice cold water and followed by extraction with methyl tea butyl ether. Evaporation gave 47.5 g of an orange oil. Vacuum distillation 0.2-16 mbar, 55-105° C. gave 2.3 g of a yellow oil which was used without further purification.

Workup

  1. stirringstirred for a further 20 minutes
  2. temperatureAfter cooling to −78° C.
  3. stirringthe mixture stirred for 10 minutes
  4. temperatureto warm to room temperature
  5. stirringwas then stirred overnight
  6. customThe reaction was quenched by gentle addition to 150 mL ice cold water
  7. extractionfollowed by extraction with methyl tea butyl ether
  8. customEvaporation

Sources & evidence

ORD record
ord-47a08459fc2f486e814f11b82f6b9120
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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