4-Toluenesulfonyl chloride → HCID 3721036, compound

HRID 336102Notes

Reaction equation

HRID 336102 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([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([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:12][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 8369Maltol

Product 1

HCID 3721036HCID 3721036, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-2-methyl-4H-pyran-4-one (0.5 g, 4.0 mmol) was reacted with p-toluenesulfonyl chloride (2.27 g, 11.9 mmol) in 40 mL of pyridine to afford PZBG-2b in 64% yield (0.71 g, 2.5 mmol). 1H NMR (500 MHz, CDCl3) δ=7.99 (d, J=8 Hz, 2H), 7.64 (d, J=5.8 Hz, 1H), 7.37 (d, J=8 Hz, 2H), 6.34 (d, J=5.8 Hz, 1H), 2.46 (s, 3H, CH3), 2.45 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3) δ=127.2, 163.2, 154.2, 145.8, 138.4, 133.6, 129.8, 129.0, 117.7, 22.0, 16.3. ESI-MS(+): m/z 281.01 [M+H]+, 303.03 [M+Na]+.

Workup

  1. customto afford PZBG-2b in 64% yield (0.71 g, 2.5 mmol)

Sources & evidence

ORD record
ord-4565e4e7538541988b05a72d2286feb5
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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