4-Toluenesulfonyl chloride → HCID 131721534, compound

HRID 991405Notes

Reaction equation

HRID 991405 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:35][CH3:36])=[C:5]([CH:32]=[CH:33][CH:34]=1)[C:6]([O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1>ClCCl>[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50]([O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:32]=[CH:33][CH:34]=[C:3]([O:2][CH3:1])[C:4]=2[O:35][CH3:36])(=[O:52])=[O:51])=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 131721535HCID 131721535, compound

Product 1

HCID 131721534HCID 131721534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 2 ( 5.0 g, 10.06 mmol) was dissolved in 50 mL of anhydrous dichloromethane and cooled to 0° C. Triethylamine (1.82 mL, 13.1 mmol) was added, followed by p-toluenesulfonyl chloride (1.92 g, 10.06 mmol) as a solid, with stirring. The reaction was stored in the refrigerator overnight. TLC Analysis indicated the reaction was approximately 80% complete. An additional 0.5 equivalents of triethylamine and 0.5 equivalents of p-toluenesulfonyl chloride were added, and the reaction was stirred at room temperature overnight. The reaction was filtered through Celite and concentrated. The residue was purified by flash chromatography using 300 mL of silica gel (wet-packed onto column using 5% triethylamine in hexane) eluting with 25-50-75% ethyl acetate in hexane containing 5% triethylamine, and then ethyl acetate containing 5% triethylamine. 5.7 g (87%) of 3 was collected as an orange oil. 1H NMR (300 MHz, CDCl3) d 7.75 (d, 2H), 7.44-7.12 (m, 11H), 6.78 (d, 4H), 4.12-4.09 (m, 2H), 3.73 (s, 6H), 3.66-3.54 (m, 13H), 3.22 (t, J=3.87 Hz, 2H), 2.41 (s, 3H).

Workup

  1. customwas stored in the refrigerator overnight
  2. stirringthe reaction was stirred at room temperature overnight
  3. filtrationThe reaction was filtered through Celite
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 25-50-75% ethyl acetate in hexane containing 5% triethylamine
  7. custom5.7 g (87%) of 3 was collected as an orange oil

Sources & evidence

ORD record
ord-0bfc75b1b9a04254bbe8ab679039faff
Source dataset
uspto-grants-2002_10
Patent number
US06465188B1

Reaction notes

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