4-Toluenesulfonyl chloride → 4-Methyl-benzenesulfinic acid 3-methoxy-propyl ester

HRID 1158449Notes

Reaction equation

HRID 1158449 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][CH2:14][CH2:15][CH2:16]O.C(N(CC)CC)C>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][O:8][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)=[O:9]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 741163-Methoxy-1-propanol

Product 1

HCID 686171304-Methyl-benzenesulfinic acid 3-methoxy-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Toluene-4-sulfonyl chloride (25.4 g, 133.2 mmol) is slowly added to a solution of 3-methoxy-1-propanol (8.49 mL, 88.8 mmol) and triethylamine (14.8 mL, 106.5 mmol) in CH2Cl2 (80 mL) at 0° C. The reaction mixture is then allowed to warm to RT and stirred for another 16 h. The solvent is evaporated, water is added and the mixture is extracted with CH2Cl2. Drying (Na2SO4) of the combined organic extracts, filtering and evaporation of the solvent affords the crude product which is purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 5:1) to give the desired product. MS (LC-MS): 262.1 [M+18]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.12 min.

Workup

  1. customThe solvent is evaporated
  2. additionwater is added
  3. extractionthe mixture is extracted with CH2Cl2
  4. dry with materialDrying (Na2SO4) of the combined organic extracts
  5. filtrationfiltering
  6. customevaporation of the solvent
  7. customaffords the crude product which
  8. customis purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 5:1)

Sources & evidence

ORD record
ord-ebb96709b5644c43a9ba926c922219af
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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