Propanal → 6,6-Diethoxy-4-hexyn-3-ol

HRID 1952623Notes

Reaction equation

HRID 1952623 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].[Li]CCCC.[CH:15](=[O:18])[CH2:16][CH3:17]>C1COCC1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][CH:15]([OH:18])[CH2:16][CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 527PropanalHCID 662853,3-DiethoxypropyneHCID 178418339Butyllithium

Product 1

HCID 664867606,6-Diethoxy-4-hexyn-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3,3-Diethoxy-propyne (2.73 g, 21.3 mmol) in THF (40 ml) was cooled to −78 C under N2. A solution of n-BuLi (2.0M in cyclohexane, 14 mL, 28 mmol) was added. After 30 min., Propionaldehyde (1.61 g, 27.7 mmol) in THF (10 ml) was added. After 15 h, the reaction was quenched by dilution with 1N HCl, warmed to room temperature and extracted into EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated to give product, 4.30 g (83%).

Workup

  1. temperaturewas cooled to −78 C under N2
  2. waitAfter 15 h
  3. customthe reaction was quenched by dilution with 1N HCl
  4. extractionextracted into EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give product, 4.30 g (83%)

Sources & evidence

ORD record
ord-8684c94532ee491293ad875553f7002f
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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