Benzenesulfonyl chloride → HCID 5220203, compound

HRID 336101Notes

Reaction equation

HRID 336101 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:10]1([S:16]([O:1][C:2]2[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=2[CH3:9])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 8369Maltol

Product 1

HCID 5220203HCID 5220203, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-2-methyl-4H-pyran-4-one (1.0 g, 7.9 mmol) was reacted with benzenesulfonyl chloride (3.0 mL, 23.7 mmol) in 75 mL of pyridine to afford PZBG-2a in 71% yield (1.50 g, 5.6 mmol). 1H NMR (500 MHz, CDCl3) δ=8.12 (d, J=8.6 Hz, 2H), 7.69 (t, J=7.5 Hz, 1H), 7.65 (d, J=5.8 Hz, 1H), 7.58 (t, J=8.0 Hz, 2H), 6.33 (d, J=5.2 Hz, 1H), 2.46 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3) δ=172.1, 163.1, 154.3, 138.4, 136.6, 134.7, 129.2, 129.0, 117.7, 16.3. ESI-MS(+): m/z 267.06 [M+H]+, 289.03 [M+Na]+.

Workup

  1. customto afford PZBG-2a in 71% yield (1.50 g, 5.6 mmol)

Sources & evidence

ORD record
ord-c02b6cad2ecb41e399e467cf5dfce52f
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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