4-Toluenesulfonyl chloride → 2H-1-Benzopyran-2-one, 4-[[(4-methylphenyl)sulfonyl]oxy]-

HRID 495144Notes

Reaction equation

HRID 495144 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C1COCC1>[O:12]=[C:4]1[CH:3]=[C:2]([O:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 546829304-Hydroxycoumarin

Product 1

HCID 108707992H-1-Benzopyran-2-one, 4-[[(4-methylphenyl)sulfonyl]oxy]-Yield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxycoumarin (30.7 mmol, 4.98 g) and triethylamine (37.3 mmol, 5.2 mL) in THF (50 mL) is cooled to (0° C.). A THF solution (50 mL) of p-toluenesulfonyl chloride (33.5 mmol, 6.45 g) is added dropwise The mixture is stirred at 0° C. for 1.5 hrs., is filtered and the solid is washed with EtOAc. The filtrate is concentrated under reduced pressure and Et2O is added. The resulting precipitate is filtered, is washed with Et2O and is dried to afford the title compound (7.57 g, 79%); 1H NMR (CDCl3, 300 MHz) δ 7.91 (2H, m), 7.61 (2H, m), 7.34 (4H, m), 6.31 (1H, s), 1.55 (3H, s); MS (ESI, Pos.) calcd for C16H12O5S m/z [M+H]=317.0, found 317.0.

Workup

  1. filtration, is filtered
  2. washthe solid is washed with EtOAc
  3. concentrationThe filtrate is concentrated under reduced pressure and Et2O
  4. additionis added
  5. filtrationThe resulting precipitate is filtered
  6. washis washed with Et2O
  7. customis dried

Sources & evidence

ORD record
ord-eeffb323e18a4c879b9383b9d2eb4952
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

Loading…