Water → HCID 18783151, compound

HRID 1636462Notes

Reaction equation

HRID 1636462 reaction equation
[CH3:1][C:2]1([CH:12]([C:18]#[N:19])C(OCC)=O)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[Li+].[Cl-].O>CS(C)=O>[C:18]([CH2:12][C:2]1([CH3:1])[CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7]1)#[N:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 22630145HCID 22630145, compound

Product 1

HCID 18783151HCID 18783151, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
155 °C

Procedure

The mixture of ethyl (1,3,3,5,5-pentamethylcyclohexyl)cyanoacetate (17) (1 g, 3,7 mmol), LiCl (0.05 g) and water (0.15 ml) in DMSO (2.5 ml) was heated at 150-160° C. for 4 h. Solution was poured into water (70 ml) and extracted with ether (4*20 ml). Ether was washed with saline (2*50 ml), dried over Na2SO4, filtered and evaporated. Crude product was purified on silica gel column, eluting with a petroleum ether--ethyl acetate mixture (20:1) to give 0.66 g (94%) of 18 as an oil. 1H NMR (CDCl3, TMS) δ: 0.98 (9H, s, 3,5-CH3eq and 1-CH3); 1.02 (6H, s, 3,5-CH3ax); 1.21 (3H, s, ring protons); 1.31 (3H, s, ring protons) and 2.31 ppm (2H, s, CH2CN). IR (neat) νCN =2242 cm1.

Workup

  1. extractionextracted with ether (4*20 ml)
  2. washEther was washed with saline (2*50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customCrude product was purified on silica gel column
  7. washeluting with a petroleum ether

Sources & evidence

ORD record
ord-e10ef037c7e34ef7a6d4dccce452f271
Source dataset
uspto-grants-2000_03
Patent number
US06034134

Reaction notes

Loading…