Isobutyraldehyde → 6,6-Diethoxy-2-methyl-hex-4-yn-3-ol

HRID 1952611Notes

Reaction equation

HRID 1952611 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:19])[CH:16]([CH3:18])[CH3:17]>C1COCC1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][CH:15]([OH:19])[CH:16]([CH3:18])[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 662853,3-DiethoxypropyneHCID 178418339Butyllithium

Product 1

HCID 130660616,6-Diethoxy-2-methyl-hex-4-yn-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3,3-Diethoxy-propyne (1.82 g, 14.2 mmol) in THF (40 ml) was cooled to −78 C under N2. A solution of n-BuLi (2.0M in cyclohexane, 9.2 mL, 18.46 mmol) was added. After 30 min, Isobutyraldehyde (1.33 g, 18.46 mmol) in THF (10 ml) was added. After 3 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, 3.18 g (100%).

Workup

  1. temperaturewas cooled to −78 C under N2
  2. waitAfter 3 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, 3.18 g (100%)

Sources & evidence

ORD record
ord-5343c2e8bb9e4c0791639958200e6e41
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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