Ethyl Acetate → 4-(Propane-1-sulfonyl)-benzaldehyde

HRID 1698503Notes

Reaction equation

HRID 1698503 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([S:13]([O-:15])=[O:14])[CH2:11][CH3:12].[Na+].C(OCC)(=O)C>CS(C)=O.CCCCCC>[CH2:10]([S:13]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:15])=[O:14])[CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 680234-FluorobenzaldehydeHCID 23706191Sodium propane-1-sulfinate

Product 1

HCID 204932624-(Propane-1-sulfonyl)-benzaldehydeYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluorobenzaldehyde (3.03 mL, 28.2 mmol) and sodium n-propylsulphinate (4.03 g, 31.0 mmol, synthesised as described in J. Med. Chem. 1989, 32, 2436) were dissolved in dry DMSO and the resulting solution heated at 100° C. for 18 h. The mixture was allowed to cool and then poured onto approximately 50 g of ice. After the ice had melted, the product was extracted into ethyl acetate (×2). The combined organic extracts were dried (MgSO4) and concentrated. Chromatography on silica eluting with 20 to 40% ethyl acetate in hexane afforded the product as a white solid (3.21 g, 54% yield). 1H NMR (400 MHz, CDCl3) 1.02 (3H, t, J=7.5 Hz), 1.72-1.82 (2H, m), 3.10-3.14 (2H, m), 8.07-8.11 (4H, m), 10.14 (1H, s).

Workup

  1. temperatureto cool
  2. extractionthe product was extracted into ethyl acetate (×2)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-682eab3a2a7c409089ed36fe08fa2701
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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