홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,4-Cyclohexadiene → N-[4-(4-Hydroxy-phenoxy)-butyl]saccharin

HRID 512021
노트
인쇄 미리보기

반응식

HRID 512021 반응식
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:19]2(=[O:21])=[O:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:19]2(=[O:21])=[O:20])=[CH:30][CH:31]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 123431,4-CyclohexadieneHCID 25018865N-[4-(4-Benzyloxy-phenoxy)-butyl]saccharin

생성물 1

HCID 25018869N-[4-(4-Hydroxy-phenoxy)-butyl]saccharin수율 56%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

To a stirred solution of 83.3 (0.1 g, 0.23 mmol) in EtOH (5 mL) was added 10% Pd/C (0.1 g, 100% w/w) and 1,4-cyclohexadiene (92 mg, 1.15 mmol) and the resulting suspension was stirred vigorously at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, the catalyst was removed by filtration through Celite, and the filtrate was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (60% diethyl ether-hexane) to give 84 (0.044 g, 56% yield) as a white solid (m p 107-109° C.). 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J=7.0 Hz, 1H), 7.92 (d, J=7.0 Hz, 1H), 7.87 (td, J=7.0 Hz, J=1.2 Hz, 1H), 7.83 (td, J=7.0 Hz, J=1.2 Hz, 1H), 6.79 (d, J=9.0 Hz, 2H), 6.74 (d, J=9.0 Hz, 2H), 4.38 (br s, 1H), 3.96 (t, J=6.4 Hz, 2H), 3.89 (t, J=7.2 Hz, 2H), 2.05 (quintet, J=6.9 Hz, 2H), 1.89 (quintet, J=6.9 Hz, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe catalyst was removed by filtration through Celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (60% diethyl ether-hexane)

출처 및 근거

ORD 기록
ord-43f34ebeeaec4617aa2e41ce8037bcf8
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102622B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트