Benzaldehyde → HCID 22559390, compound

HRID 984537Notes

Reaction equation

HRID 984537 reaction equation
[Li+].[I-].[CH:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:12]([CH3:23])[C:13](=[O:22])[C:14]([CH3:21])([CH3:20])[CH:15]([O:18][CH3:19])[O:16][CH3:17]>C1COCC1>[OH:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:12]([CH3:23])[C:13](=[O:22])[C:14]([CH3:20])([CH3:21])[CH:15]([O:16][CH3:17])[O:18][CH3:19]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 66321Lithium iodideHCID 22559378HCID 22559378, compound

Product 1

HCID 22559390HCID 22559390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 298 mg (2.42 mmol) CrCl2 and 20 mg (0.15 mmol) LiI in 6.0 mL abs. THF were added 117 μl (1.1 mmol) benzaldehyde and 253 mg (1.0 mmol) 4-bromo-1,1-dimethoxy-2,2-dimethyl-pentan-3-one (225). After stirring at ambient temperature for 30 minutes the brown solution was quenched with 5.0 mL brine. The aqueous phase was extracted three times with 5.0 mL diethylether. The organic layers were combined, washed with conc. NH4C, solution (2×5.0 mL), dried over MgSO4, filtrated and concentrated in vacuo. The remaining green oil (196 mg) was purified via flash chromatography (column dimensions: 3.5×20.0 cm, ethyl acetate/petroleum ether=1:6).

Workup

  1. customwas quenched with 5.0 mL brine
  2. extractionThe aqueous phase was extracted three times with 5.0 mL diethylether
  3. washwashed with conc. NH4C, solution (2×5.0 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe remaining green oil (196 mg) was purified via flash chromatography (column dimensions: 3.5×20.0 cm, ethyl acetate/petroleum ether=1:6)

Sources & evidence

ORD record
ord-3eab347fe2044505978304a661307e36
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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