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

HRID 1977975Notes

Reaction equation

HRID 1977975 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) 3-[3-(2-chlorophenylsulfonyloxy)-5-methylphenoxy]propanol, as prepared according to step c of Example 1, 411 μL (3.23 mmol) of N,N-diisopropylethylamine, and 230 μL (3.0 mmol) of dimethylsulfoxide in dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 h and then quenched with 10% 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) δ9.83 (t, 1H, J=1.4 Hz), 7.97 (dd, 1H), 7.56-7.65 (m, 2H), 7.35-7.42 (m, 1H), 6.60 (br s, 1H), 6.57 (br s, 1H), 6.49 (br s, 1H), 4.19 (t, 2H, J=6.1 Hz), 2.86 (dt, 2H, J=6, 1.4 Hz), and 2.25 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-d173c8c393854260a179c0eeee6c4528
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

Loading…