Sodium Cyanide → HCID 178458837, compound

HRID 2291232Notes

Reaction equation

HRID 2291232 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([CH2:16]Cl)[C:9]=2[CH3:18])[CH2:5][C:4](=[O:19])[C:3]=1[C:20](=[O:23])[CH2:21][CH3:22].[C-:24]#[N:25].[Na+]>>[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([CH2:16][C:24]#[N:25])[C:9]=2[CH3:18])[CH2:5][C:4](=[O:19])[C:3]=1[C:20](=[O:23])[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 8929Sodium CyanideHCID 178458836HCID 178458836, compound

Product 1

HCID 178458837HCID 178458837, compoundYield 81.8%

Procedure

A solution of 3-hydroxy 2-propionyl-5-(3-chloromethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (3.32, 9.96 mmol) in dmf (15 ml) was added to a suspension of sodium cyanide (0.98, 19.9 mmol) in dmf (10 ml). The mixture was stirred at 70° for 4 h, then cooled and partitioned between methylene choride and water. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel (elution with an increasing gradient of ethyl acetate in methylene chloride) gave 3-hydroxy-2-propionyl-5-(3-cyanomethyl-2,4,6-trimethylphenyl) cyclohex-2-en-1-one (2.65 g, 81%) plus a further impure fraction. Proton magnetic resonance spectrum (CDCl3, δ in ppm): 1.18 (3H,t,J7 Hz); 2.33 (3H,s); 2.37 (3H,s); 2.42 (3H,s); 2.5-4.1(7H,m); 3.62 (2H,s); 7.90 (1H,s); 18.20 (1H,s). Infrared spectrum: ν (CHCl3) 2250 m cm-1.

Workup

  1. temperaturecooled
  2. custompartitioned between methylene choride and water
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washChromatography on silica gel (elution with an increasing gradient of ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-a5c4cd2d3d0e4937bf9de91fa957f008
Source dataset
uspto-grants-1989_01
Patent number
US04795487

Reaction notes

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