Maltol → 2-Methyl-4-oxo-4H-pyran-3-yl 2,4-dinitrobenzenesulfonate

HRID 336104

반응식

HRID 336104 반응식
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[N+:10]([C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[S:22](Cl)(=[O:24])=[O:23])([O-:12])=[O:11]>N1C=CC=CC=1>[N+:10]([C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[S:22]([O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9])(=[O:24])=[O:23])([O-:12])=[O:11]

참가 물질

4

반응물 2

HCID 8369MaltolHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-

생성물 1

HCID 866603532-Methyl-4-oxo-4H-pyran-3-yl 2,4-dinitrobenzenesulfonate수율 28%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3-Hydroxy-2-methyl-4H-pyran-4-one (0.5 g, 4.0 mmol) was reacted with 2,4-dinitrobenzenesulfonyl chloride (1.58 g, 5.9 mmol) in 40 mL of pyridine to afford PZBG-2d in 28% yield (0.39 g, 1.1 mmol). 1H NMR (500 MHz, CDCl3) δ=8.72 (d, J=2.3 Hz, 1H), 8.56 (dd, J1=9.2 Hz, J2=2.3 Hz, 1H), 8.44 (d, J=8.6 Hz, 1H), 7.71 (d, J=5.8 Hz, 1H), 6.31 (d, J=5.8 Hz, 1H), 2.53 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3) δ=171.6, 163.3, 154.9, 139.3, 136.4, 133.8, 126.8, 120.5, 117.5, 16.1. ESI-MS(+): m/z 357.03 [M+H]+, 378.99 [M+Na]+.

후처리

  1. customto afford PZBG-2d in 28% yield (0.39 g, 1.1 mmol)

출처 및 근거

ORD 기록
ord-7c859e0316b6449e901226fffaf94e89
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889638B2

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