4-Toluenesulfonyl chloride → 5-((Tetrahydro-2H-pyran-2-yl)oxy)pent-2-yn-1-yl 4-methylbenzenesulfonate

HRID 638132Notes

Reaction equation

HRID 638132 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][OH:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[OH-].[K+]>CCOCC>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:13][CH2:12][C:11]#[C:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 110414015-(Tetrahydro-pyran-2-yloxy)-pent-2-yn-1-ol

Product 1

HCID 112446535-((Tetrahydro-2H-pyran-2-yl)oxy)pent-2-yn-1-yl 4-methylbenzenesulfonateYield 99.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of alcohol 8 (6.16 g, 33.5 mmol) and p-toluenesulphonyl chloride (7.36 g, 38.5 mmol) in dry ether (80 mL) was cooled to -10°. Powdered KOH (25 g, 446 mmol) was added in 5 g portions over 20 min. The resulting suspension was stirred at 0° for 45 min, poured into ice-water (200 mL) and extracted with ether (3×100 mL). The combined ether solutions were washed with brine, dried (MgSO4), and concentrated in vacuo. Final traces of solvent were removed by pumping for 6 hr at 0.1 mmHg, yielding 11.23 g of 9 (99%). This was used without further purification.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe combined ether solutions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customwere removed
  6. waitby pumping for 6 hr at 0.1 mmHg

Sources & evidence

ORD record
ord-cc3051340a954f9cb71a0cbb831b434e
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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