Dimethyl Sulfoxide → 3-[5-Methyl-3-(3-pyridinylsulfonyloxy)phenoxy]propionaldehyde
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH:10]=[O:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
At 0° C. to a solution of 276 mg (0.855 mmol) of 3-[5-methyl-3-(3-pyridinylsulfonyloxy)phenoxy]propanol, as prepared in the preceding step, in anhydrous dichloromethane (2 mL) containing 450 μL (2.58 mmol) of N,N-diisopropylethylamine and 92 μL (1.19 mmol) of anhydrous dimethyl sulfoxide was added 204 mg (1.28 mmol) of sulfur trioxide pyridine complex. The reaction mixture was stirred at 0° C. for 30 min, diluted with 20 mL of toluene, and concentrated to an oil which was used directly in the next reaction.
Workup
- additionwas added 204 mg (1.28 mmol) of sulfur trioxide pyridine complex
- concentrationconcentrated to an oil which
- customwas used directly in the next reaction
Sources & evidence
- ORD record
- ord-05f527929c67499e84a3565983b7d0d2
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05891909
Reaction notes
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