Isobutyraldehyde → HCID 22559404, compound

HRID 984538Notes

Reaction equation

HRID 984538 reaction equation
[Li+].[I-].[CH3:3][CH:4]([CH:6]=[O:7])[CH3:5].Br[CH:9]([CH3:20])[C:10](=[O:19])[C:11]([CH3:18])([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14]>C1COCC1>[OH:7][CH:6]([CH:4]([CH3:5])[CH3:3])[CH:9]([CH3:20])[C:10](=[O:19])[C:11]([CH3:18])([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 66321Lithium iodideHCID 22559378HCID 22559378, compound

Product 1

HCID 22559404HCID 22559404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 298 mg (2.42 mmol) CrCl2 and 29 mg (0.22 mmol) LiI in 6.0 mL abs. THF were added 100 μl (1.1 mmol) isobutyric aldehyde and 253 mg (1.0 mmol) 4-bromo-1,1-dimethoxy-2,2-dimethyl-pentan-3-one (225). After stirring at ambient temperature for one hour the brown solution was quenched with 5.0 mL brine. The aqueous phase was extracted three times with 5.0 mL of a diethylether-pentane mixture (5:1). The organic layers were combined, washed with conc. NH4Cl solution (3×5.0 mL), dried over MgSO4, filtrated and concentrated in vacuo. The remaining colourless oil (206 mg) was purified via flash chromatography (column dimensions: 3.5×20.0 cm, ethyl acetate/petroleum ether=1:8).

Workup

  1. customwas quenched with 5.0 mL brine
  2. extractionThe aqueous phase was extracted three times with 5.0 mL of a diethylether-pentane mixture (5:1)
  3. washwashed with conc. NH4Cl solution (3×5.0 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe remaining colourless oil (206 mg) was purified via flash chromatography (column dimensions: 3.5×20.0 cm, ethyl acetate/petroleum ether=1:8)

Sources & evidence

ORD record
ord-b8c72a5b69a14005beb668d3ea09f1fe
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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