Benzenesulfonyl chloride → 7-Oxocyclohepta-1,3,5-trien-1-yl benzenesulfonate

HRID 336109

반응식

HRID 336109 반응식
[OH:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1.[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:9][C:3]2[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 10789Tropolone

생성물 1

HCID 866603587-Oxocyclohepta-1,3,5-trien-1-yl benzenesulfonate수율 76%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

2-Hydroxycyclohepta-2,4,6-trienone (0.2 g, 1.7 mmol) was reacted with benzenesulfonyl chloride (0.63 mL, 4.9 mmol) in 5 mL of pyridine to afford PZBG-4a in 76% yield (0.33 g, 1.3 mmol). 1H NMR (400 MHz, DMSO) δ=7.95 (d, J=7.6 Hz, 2H), 7.80 (t, J=7.6 Hz, 1H), 7.67 (t, J=8 Hz, 2H), 7.43-7.37 (m, 2H), 7.25 (t, J=8.4 Hz, 1H), 7.14-7.09 (m, 2H). 13C NMR (100 MHz, CDCl3) δ=179.24, 154.79, 141.19, 138.21, 136.37, 136.33, 135.57, 131.96, 130.92, 130.27, 128.76. ESI-MS(+): m/z 262.97 [M+H]+, 279.72 [M+NH4]+, 284.99 [M+Na]+.

후처리

  1. customto afford PZBG-4a in 76% yield (0.33 g, 1.3 mmol)

출처 및 근거

ORD 기록
ord-7275e09284a74c7abd330506c8043c1c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889638B2

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