Hydrochloric Acid → HCID 59496759, compound

HRID 449449Notes

Reaction equation

HRID 449449 reaction equation
[C-:1]#[N:2].[K+].[C:4]1(=[C:8]2[C:13](=[O:14])[O:12][C:11]([CH3:16])([CH3:15])[O:10][C:9]2=[O:17])[CH2:7][CH2:6][CH2:5]1.Cl>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(O)C>[CH3:16][C:11]1([CH3:15])[O:12][C:13](=[O:14])[CH:8]([C:4]2([C:1]#[N:2])[CH2:5][CH2:6][CH2:7]2)[C:9](=[O:17])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 594965465-Cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 59496759HCID 59496759, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Potassium cyanide (0.12 g, 1.8 mmol) was added to a mixture of 5-cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (0.30 g, 1.5 mmol) and tetra-N-butylammonium bromide (0.049 g, 0.15 mmol) (Sigma-Aldrich, Cat. #193119) in ethanol (5.0 mL). The reaction mixture was stirred at 80° C. for 2 h. After cooled to r.t., the mixture was adjusted to pH=2 with aqueous HCl. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%) to afford the desired product (0.32 g, 94%).

Workup

  1. temperatureAfter cooled to r.t.
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in dichloromethane (0-80%)

Sources & evidence

ORD record
ord-c67ce501b9654c068116e46837b5938b
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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