Water → HCID 18783151, compound

HRID 1420877Notes

Reaction equation

HRID 1420877 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) (1g, 3,7 mmol), LiCl (0.05 g) and water (0.15 ml) in DMSO (2.5ml) 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.

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-ethyl acetate mixture (20:1)

Sources & evidence

ORD record
ord-7e5e237c56b24af48562d7976e113cad
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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