Sodium Hydroxide → 3-Cyclopentylpropiolonitrile

HRID 1524676Notes

Reaction equation

HRID 1524676 reaction equation
[CH:1]1([C:6]#[CH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.C1(O[C:20]#[N:21])C=CC=CC=1.[OH-].[Na+]>C1COCC1.CCCCCC>[CH:1]1([C:6]#[C:7][C:20]#[N:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70740Phenyl cyanateHCID 136725CyclopentylacetyleneHCID 178418339Butyllithium

Product 1

HCID 574776163-CyclopentylpropiolonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of cyclopentylacetylene (0.50 g, 5.3 mmol) in THF (5 mL) at −78° C. was added 2.5 M n-butyllithium in hexane (2.23 mL). The mixture was stirred for 15 min followed by the dropwise addition of phenyl cyanate (0.70 g, 5.8 mmol) in THF (3 mL). The reaction was warmed to room temperature. Into the reaction mixture was poured 6 N NaOH, and the mixture was stirred for 5 minutes. The product was extracted with diethyl ether. The extracts were washed with 6 N NaOH and with brine, then dried over sodium sulfate, decanted and the solvent was removed in vacuo to afford product (600 mg, 95%). 1H NMR (300 MHz, CDCl3): δ 2.81-2.68 (m, 1H), 2.07-1.54 (m, 8H).

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. extractionThe product was extracted with diethyl ether
  3. washThe extracts were washed with 6 N NaOH and with brine
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0891fb8f7e524325a906bcf6468ba8e2
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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