3-(Methylsulfonyl)benzaldehyde → 1-(3-Methanesulfonylphenyl)ethan-1-ol

HRID 415358Notes

Reaction equation

HRID 415358 reaction equation
[CH3:1][Mg]I.[CH3:4][S:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])(=[O:7])=[O:6]>C1COCC1>[CH3:4][S:5]([C:8]1[CH:9]=[C:10]([CH:11]([OH:12])[CH3:1])[CH:13]=[CH:14][CH:15]=1)(=[O:6])=[O:7]

Participants

4

Reactant 2

HCID 135966023-(Methylsulfonyl)benzaldehydeHCID 178418373HCID 178418373, compound

Product 1

HCID 666231181-(3-Methanesulfonylphenyl)ethan-1-olYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium iodide (3M in THF, 13.2 mL, 4.4 mmol) was added dropwise via syringe at 0° C. to 3-(methylsulfonyl)benzaldehyde (0.74 g, 4.0 mmol) in THF (15 mL). The resulting reaction mixture was stirred at 0° C. until no more conversion to product occurred (monitored by GC-MS). The reaction was quenched with saturated ammonium chloride, the aqueous phase was extracted with EtOAc and the organic phase was washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (EtOAc:hexane 1:4) to give the title compound (260 mg) that was used in the next step without any further purification (approximate purity 50%).

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with saturated ammonium chloride
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washthe organic phase was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash column chromatography on silica (EtOAc:hexane 1:4)

Sources & evidence

ORD record
ord-734f6ed163bf4b4fa6546a95fc03b2cc
Source dataset
uspto-grants-2012_01
Patent number
US08088780B2

Reaction notes

Loading…