HCID 86612272, compound → HCID 66917402, compound

HRID 2355211Notes

Reaction equation

HRID 2355211 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]=[O:19])=[C:12]([Br:20])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][Si:22]([CH2:25][Mg]Cl)([CH3:24])[CH3:23]>C1COCC1>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]([OH:19])[CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:12]([Br:20])[CH:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 86612272HCID 86612272, compoundHCID 178418680HCID 178418680, compound

Product 1

HCID 66917402HCID 66917402, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-benzenesulfonyl-2-bromo-phenyl)-propionaldehyde (4.77 g, 13.5 mmol) in THF (40 mL) was added trimethylsilylmethylmagnesium chloride (1M in Et2O, 27.3 mL) at −78° C. under Argon atmosphere. The reaction was allowed to reach 0° C. and was stirred for 3 hours, then quenched by addition of buffer pH=2 KHSO4/Na2SO4 (10%) at 0° C. The mixture was extracted 3 times with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 8/2) to afford 4-(4-benzenesulfonyl-2-bromo-phenyl)-1-trimethylsilanyl-butan-2-ol (4.60 g, 77% yield).

Workup

  1. customto reach 0° C.
  2. customquenched by addition of buffer pH=2 KHSO4/Na2SO4 (10%) at 0° C
  3. extractionThe mixture was extracted 3 times with EtOAc
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified via flash chromatography (hexane/EtOAc, 8/2)

Sources & evidence

ORD record
ord-4cf0135246ca443e8da91979295ca251
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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