Sodium Cyanide → HCID 66651716, compound

HRID 418909Notes

Reaction equation

HRID 418909 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15]OC1C(C)=CC(C)=CC=1C.[C-:26]#[N:27].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][C:26]#[N:27]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 66652048HCID 66652048, compound

Product 1

HCID 66651716HCID 66651716, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Combine 2-[2-(2-methoxy-phenyl)-cyclohexylmethoxy]-1,3,5-trimethyl-benzene (0.810 g, 2.71 mmol), sodium cyanide (2.13 g, 43.4 mmol), and d6-DMSO (10.0 mL) at rm temperature. Heat and stir at 100° C. under nitrogen for 18 hours. Cool to room temperature and add ethyl acetate then add water and wash 5× with brine. Separate layers and dry over anhydrous sodium sulfate. Concentrate and flash chromatography using 0 to 30% ethyl acetate/hexanes to yield the titled compound (0.346 g, 56%). TLC Rf=0.43 in 20% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 1H), 7.0 (m, 1H), 6.9 (m, 2H), 3.8 (s, 3H), 3.3 (m, 1H), 2.5 (m, 1H), 2.3 (m, 1H), 2.1 (m, 1H), 1.8 (m, 6H), 1.4 (m, 2H).

Workup

  1. temperatureHeat
  2. temperatureCool to room temperature
  3. washadd water and wash 5× with brine
  4. dry with materialSeparate layers and dry over anhydrous sodium sulfate
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-36c7bca159d0415a826d2bdb5077a315
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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