2-Cyclohexylidenemalononitrile → HCID 86665182, compound

HRID 1912950Notes

Reaction equation

HRID 1912950 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[C:5]1(=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C1COCC1>[CH:1]([C:5]1([CH:11]([C:12]#[N:13])[C:14]#[N:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[CH2:2]

Participants

4

Reactant 2

HCID 203652-CyclohexylidenemalononitrileHCID 178418507HCID 178418507, compound

Product 1

HCID 86665182HCID 86665182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of vinylmagnesium bromide (1 M in THF, 24 mL, 24 mmol) was added dropwise over 2 min to a solution of the product from Example 145A (730 mg, 4.99 mmol) in THF (8 mL) under nitrogen. The reaction mixture was stirred at room temperature for 13 hours, then quenched by cautious addition of saturated aqueous NH4Cl (25 mL). The mixture was stirred vigorously for 10 minutes, and then diluted with water (10 mL). The aqeuous layer was separated and extracted with EtOAc (25 mL). The combined organic phase was concentrated under vacuum, and the residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc, 90:10-80:20) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.24-1.37 (m, 2H), 1.40-1.68 (m, 6H), 1.85-2.03 (m, 2H), 3.56 (s, 1H), 5.39 (d, J=17.4 Hz, 1H), 5.53 (d, J=10.7 Hz, 1H), 5.73 (dd, J=17.5, 10.7 Hz, 1H).

Workup

  1. customquenched by cautious addition of saturated aqueous NH4Cl (25 mL)
  2. stirringThe mixture was stirred vigorously for 10 minutes
  3. additiondiluted with water (10 mL)
  4. customThe aqeuous layer was separated
  5. extractionextracted with EtOAc (25 mL)
  6. concentrationThe combined organic phase was concentrated under vacuum
  7. customthe residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc, 90:10-80:20)

Sources & evidence

ORD record
ord-4e89d7015a144472a4bff785f57d26ed
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…