4-Toluenesulfonyl chloride → pent-4-ynyl tosylate

HRID 606049Notes

Reaction equation

HRID 606049 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.[CH2:12]([OH:17])[CH2:13][CH2:14][C:15]#[CH:16].C(N(CC)CC)C>ClCCl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:17][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 793464-Pentyn-1-ol

Product 1

HCID 10966564pent-4-ynyl tosylateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

p-Toluenesulfonyl chloride (21.4 g, 112 mmol) was added slowly to a stirred solution of 4-pentyn-1-ol (11.5 mL, 124 mL) and triethylamine (17.2 mL, 124 mmol) in dichloromethane (100 mL) at room temperature. After 22 hours, the solution was diluted with dichloromethane, washed with water, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 95:5 to 85:15 hexanes/ethyl acetate) to afford the product pent-4-ynyl 4-methylbenzenesulfonate (23.4 g, 87%) as a colorless oil.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 95:5 to 85:15 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cb613e99fa82443e9122e343e7d282e5
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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