4-Toluenesulfonyl chloride → HCID 22320763, compound

HRID 395381Notes

Reaction equation

HRID 395381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:12][CH2:11][CH2:10][C:9]#[C:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 223207605-(4-Chlorophenyl)pent-4-yn-1-ol

Product 1

HCID 22320763HCID 22320763, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

5-(4-Chlorophenyl)pent-4-yn-1-ol (35.7 g, 182 mmol), 4-dimethylaminopyridine (8.9 g, 73 mmol), p-toluenesulfonyl chloride (34.7 g, 182 mmol), and 62 ml of triethylamine were combined in 330 ml of dichloromethane at 0° C. The mixture was stirred for 30 min. at 0° then 18 hours at room temperature. Dilution with 200 ml of dichloromethane followed by washing with brine, drying over magnesium sulfate, filtration through silica gel with hexane-ethyl acetate, 8:1, gave a yellow solid on evaporation. Crystallization from ether gave 5-(4-Chlorophenyl)pent-4-yn-1-ol p-toluenesulfonate as colorless crystals (31.7 g, 49% yield). This was converted to the title compound by reaction with sodium iodide in acetone, and was used in subsequent reactions with no further purification; MS m/z 303.9 (M+ calcd. for C11H10ClI=304.6).

Workup

  1. custom18 hours
  2. customat room temperature
  3. washby washing with brine
  4. dry with materialdrying over magnesium sulfate, filtration through silica gel with hexane-ethyl acetate, 8:1
  5. customgave a yellow solid
  6. customon evaporation
  7. customCrystallization from ether

Sources & evidence

ORD record
ord-79327c072d464ec19a1d4af6ec463dd6
Source dataset
uspto-grants-2003_08
Patent number
US06605628B1

Reaction notes

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