Dimethyl Sulfoxide → 3-[3-(5-Chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442943Notes

Reaction equation

HRID 442943 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:11])=[O:10].CS(C)=O.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 540486313-[3-(5-Chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 536659503-[3-(5-Chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenoxy]propionaldehydeYield 30.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 227 mg (0.660 mmol) of 3-[3-(5-chloro-1,3-dimethyl-pyrazole-4-sulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, in dichloromethane (2 mL) containing 61 μL (0.79 mmol) of anhydrous dimethyl sulfoxide and 275 μL (1.58 mmol) of N,N-diisopropylethylamine was added 124 mg (0.78 mmol) of sulfur trioxide pyridine complex. The reaction mixture was stirred at ambient temperature for 60 min and then purified by flash chromatography (dichloromethane then 20% ethyl acetate/dichloromethane) to give 75 mg of the title compound as an unstable oil. TLC clearly showed 3-(5-chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenol as the major byproduct. 1H-NMR (300 MHz, CDCl3) δ 9.85 (t, 1H, J=1.5 Hz), 6.64 (s, 1H), 6.51-6.57 (m, 2H), 6.46 (t, 1H, J=2 Hz), 6.42 (t, 1H, J=2 Hz), 4.23 (t, 2H, J=6 Hz), 3.82 (s, 3H), 2.89 (td, 2H, J=1, 6 Hz), 2.29 (s, 3H), 2.26 (s, 3H).

Workup

  1. additionwas added 124 mg (0.78 mmol) of sulfur trioxide pyridine complex
  2. custompurified by flash chromatography (dichloromethane

Sources & evidence

ORD record
ord-fabb43b91a324a2aaa2f5ef00a40e0a4
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…