Hydrochloric Acid → HCID 14271911, compound

HRID 1906776Notes

Reaction equation

HRID 1906776 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].[CH2:13]([OH:16])[C:14]#[CH:15].Cl>O1CCCC1>[CH2:13]([O:16][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]#[CH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 14271911HCID 14271911, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of ethyl 4-chloroacetoacetate (294 g) in tetrahydrofuran (200 ml) was added over 3 hours to a stirred, ice-cooled suspension of sodium hydride (150 g of a 80% dispersion in mineral oil) in tetrahydrofuran (500 ml) at such a rate than the reaction temperature remained ≤20°. A solution of prop-2-ynol (100 g) in tetrahydrofuran (200 ml) was then added over 2 hours to the above mixture with stirring and ice-cooling at such a rate that the reaction temperature never exceeded +25°. The mixture was then stirred at room temperature for 16 hours, poured into 2M HCl (900 ml) and the layers separated. The organic layer was evaporated and the resulting red oil was separated in a separating funnel from the mineral oil. The red oil was taken up in dichloromethane and the resulting solution was washed several times with water, dried over Na2SO4 and evaporated to give the title compound (313 g) as a dark oil which was used directly in Preparation 3.

Workup

  1. temperaturecooled
  2. customremained ≤20°
  3. temperatureice-cooling at such a rate that the reaction temperature never exceeded +25°
  4. stirringThe mixture was then stirred at room temperature for 16 hours
  5. customthe layers separated
  6. customThe organic layer was evaporated
  7. customthe resulting red oil was separated in a separating funnel from the mineral oil
  8. washthe resulting solution was washed several times with water
  9. dry with materialdried over Na2SO4
  10. customevaporated

Sources & evidence

ORD record
ord-63fb153789ba4e71b3bc896887a82ae9
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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