4-Iodobenzaldehyde → HCID 66762205, compound

HRID 573771Notes

Reaction equation

HRID 573771 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11]>C(OCC)C.O1CCCC1>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 966574-IodobenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 66762205HCID 66762205, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g 4-Iodobenzaldehyde are dissolved in 25 ml diethylether, cooled to 0° C. and treated dropwise with 6.0 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane. The temperature is slowly raised to room temperature and the mixture is stirred for further 12 hours. Then the reaction is quenched by addition of half saturated aqueous ammonium chloride. The aqueous phase is twice extracted with ethylacetate and the combined organic phases are washed twice with saturated aqueous ammonium chloride and brine. After drying with magnesium sulphate the solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 100:0 to 40:60).

Workup

  1. temperatureThe temperature is slowly raised to room temperature
  2. customThen the reaction is quenched by addition of half saturated aqueous ammonium chloride
  3. extractionThe aqueous phase is twice extracted with ethylacetate
  4. washthe combined organic phases are washed twice with saturated aqueous ammonium chloride and brine
  5. dry with materialAfter drying with magnesium sulphate the solvents
  6. customare evaporated in vacuo
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 100:0 to 40:60)

Sources & evidence

ORD record
ord-8085396aee2244138180a45be1293341
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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