4-Toluenesulfonyl chloride → HCID 18471598, compound

HRID 1383869Notes

Reaction equation

HRID 1383869 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:4][CH:3]=1.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>CN(C)C1C=CN=CC=1.ClCCl>[S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11704664HCID 11704664, compound2×

Product 1

HCID 18471598HCID 18471598, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 15-(p-iodophenyl)pentadecanol (Compound II) (200 mg; 0.47 mmol), tosyl chloride (102 mg; 0.53 mmol) and 4-dimethylaminopyridine (66 mg; 0.53 mmol) in dichloromethane (3 ml) was stirred at room temperature for 12 h. The reaction mixture was then partitioned between chloroform (40 ml), methanol (40 ml) and 0.1 N hydrochloric acid (36 ml). The chloroform layer was separated and extraction was repeated (2×40 ml of chloroform). Extracts were combined, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel in hexane-chloroform (from 95:5 to 40:60) to give Compound III, 15-(p-Iodophenyl)pentadecyl tosylate (259 mg, 95%).

Workup

  1. customThe reaction mixture was then partitioned between chloroform (40 ml), methanol (40 ml) and 0.1 N hydrochloric acid (36 ml)
  2. customThe chloroform layer was separated
  3. extractionextraction
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel in hexane-chloroform (from 95:5 to 40:60)

Sources & evidence

ORD record
ord-3d39056899ef4db389aed0f935eae95c
Source dataset
uspto-grants-2001_07
Patent number
US06255519B1

Reaction notes

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