Sodium Cyanide → HCID 90414479, compound

HRID 1776714Notes

Reaction equation

HRID 1776714 reaction equation
[C:1](/[C:3](=[C:9]1\[CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][CH2:13]\1)/C(OCC)=O)#[N:2].[C-:16]#[N:17].[Na+]>CCO>[C:1]([CH2:3][C:9]1([C:16]#[N:17])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[CH2:10]1)#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 131733023HCID 131733023, compound

Product 1

HCID 90414479HCID 90414479, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottomed flask equipped with a stir bar and a reflux condenser, containing (E)-ethyl 2-cyano-2-(3,3-dimethylcyclopentylidene)acetate (9.5 g, 46 mmol) in EtOH (50 mL), was added sodium cyanide (2.3 g, 46 mmol). The reaction mixture was refluxed for 24 h, cooled to RT and concentrated to dryness. The residue was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organics was dried with Na2SO4, concentrated to dryness and subjected to FCC to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 2.75 (s, 2H), 2.41-2.33 (m, 1H), 2.19 (d, J=15 Hz, 1H), 2.03-1.93 (m, 1H), 1.85-1.63 (m, 3H), 1.20 (s, 3H), 1.11 (s, 3H).

Workup

  1. customTo a round bottomed flask equipped with a stir bar and a reflux condenser
  2. temperatureThe reaction mixture was refluxed for 24 h
  3. concentrationconcentrated to dryness
  4. additionThe residue was diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organics was dried with Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f7a0987c150d49fa85e51c48e8fb419b
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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