Hydrochloric Acid → HCID 21934987, compound

HRID 1241460Notes

Reaction equation

HRID 1241460 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.[C:9](#[N:12])[CH:10]=[CH2:11].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.Cl>O1CCOCC1>[CH:7]([C:4]1([CH2:11][CH2:10][C:9]#[N:12])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 21934987HCID 21934987, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tetrahydro-2H-pyran-4-carbaldehyde (1.0 g, 8.77 mmol) and acrylonitrile (0.6 mL, 8.77 mmol) in dioxane (5 mL) was cooled to 0° C., treated with benzyltrimethylammonium hydroxide (0.04 mL, 40% in methanol), stirred at 0° C. for 30 minutes, warmed to room temperature, and stirred for 18 hours. The mixture was neutralized with 1N HCl and extracted with ethyl acetate. The organic phase was washed with aqueous saturated NaHCO3, dried (Na2SO4), filtered, and concentrated. The oil was purified by flash chromatography eluting with 0% to 50% ethyl acetate/hexane to provide the desired product as a colorless oil (0.777 g, 53% yield).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with aqueous saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe oil was purified by flash chromatography
  9. washeluting with 0% to 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b2730417c35f47c1bb38da555a325e19
Source dataset
uspto-grants-2006_10
Patent number
US07115601B2

Reaction notes

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