4-Toluenesulfonyl chloride → HCID 15428282, compound

HRID 368779Notes

Reaction equation

HRID 368779 reaction equation
[OH:1][C@H:2]([C@H:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>C([Sn](=O)CCCC)CCC.C(Cl)Cl>[S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)([O:4][CH2:3][C@H:2]([OH:1])[C@H:5]([CH3:14])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11063306HCID 11063306, compound

Product 1

HCID 15428282HCID 15428282, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 2 L 3-neck round-bottom flask equipped with a mechanical stirrer and nitrogen inlet was added diol 17 (58 g, 0.30 mol), dibutyltin oxide (1.5 g, 0.006 mol, 2 mol %), p-toluenesulfonyl chloride (57.5 g, 0.30 mol), CH2Cl2 (580 mL) and triethylamine (42.0 mL, 0.30 mol). The resulting mixture was stirred at room temperature for 2 h (although the reaction was complete within 1 h), filtered, washed with water and dried over MgSO4. Concentration of the volatiles in vacuo afforded the title compound (104.1 g) as a slightly amber oil.

Workup

  1. customTo a 2 L 3-neck round-bottom flask equipped with a mechanical stirrer and nitrogen inlet
  2. waitwas complete within 1 h
  3. filtration), filtered
  4. washwashed with water
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-6d23fbaaf6d740a5af503390ef183d00
Source dataset
uspto-grants-2000_10
Patent number
US06133457

Reaction notes

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