Dimethyl Sulfoxide → 3-[3-(2-Chlorophenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442893Notes

Reaction equation

HRID 442893 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[O:15][CH2:16][CH2:17][CH2:18][OH:19])(=[O:10])=[O:9].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[O:15][CH2:16][CH2:17][CH:18]=[O:19])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 114850963-[3-(2-Chlorophenylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 227226393-[3-(2-Chlorophenylsulfonyloxy)-5-methylphenoxy]propionaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfur trioxide pyridine complex (847 mg, 5.36 mmol) was added to a solution of 619 mg (1.74 mmol) of 3-[3-(2-chlorophenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared in the preceding step, 411 μL (3.23 mmol) of N,N-diisopropylethylamine, and 230 μL (3.0 mmol) of anhydrous dimethyl sulfoxide in anhydrous dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 h and then quenched with 10% aqueous citric acid (20 mL). The reaction mixture was extracted with diethyl ether (3×30 mL), dried (MgSO4), and purified by flash chromatography (diethyl ether/petroleum ether (2:1 to 4:1)) to afford 289 mg (47% yield) of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 9.83 (t, 1 H, J=1.4 Hz), 7.97 (dd, 1 H), 7.56-7.65 (m, 2 H), 7.35-7.42 (m, 1 H), 6.60 (br s, 1 H), 6.57 (br s, 1 H), 6.49 (br s, 1 H), 4.19 (t, 2 H, J=6.1 Hz), 2.86 (td, 2 H, J=1.4, 6 Hz), and 2.25 (s, 3 H).

Workup

  1. customquenched with 10% aqueous citric acid (20 mL)
  2. extractionThe reaction mixture was extracted with diethyl ether (3×30 mL)
  3. dry with materialdried (MgSO4)
  4. custompurified by flash chromatography (diethyl ether/petroleum ether (2:1 to 4:1))

Sources & evidence

ORD record
ord-55f40dd4a4384bd5941e4c6411e1b82f
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…