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Dabco → dimethyl-thiocarbamic acid O-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenyl}ester

HRID 1157258
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HRID 1157258 반응식
[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([OH:16])=[C:11]([Cl:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].N12CCN(CC1)CC2.[CH3:38][N:39]([CH3:43])[C:40](Cl)=[S:41]>CN(C)C=O.C(OCC)(=O)C>[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][C:40](=[S:41])[N:39]([CH3:43])[CH3:38])=[C:11]([Cl:17])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 684439204-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-2,6-dichlorophenol

생성물 1

HCID 86610366dimethyl-thiocarbamic acid O-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenyl}ester수율 90.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A solution of 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol (70) (289 mg, 0.78 mmol) in N,N-dimethylformamide (4 mL) at 25° C. was treated with 1,4-diazabicyclo[2.2.2]octane (172 μL, 1.56 mol) and dimethylthiocarbamoyl chloride (154 mg, 1.25 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with ethyl acetate and was then washed with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95:5 petroleum ether/ethyl acetate) afforded dimethyl-thiocarbamic acid O-{4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenyl}ester (71) (376 mg, 90%) as a white solid; EI(+)-HRMS m/e calcd for C27H31Cl2N2O2SSi (M+H)+ 532.1295, found 532.1292. Exact Mass=531.1222; Molecular weight=532.61

후처리

  1. washwas then washed with a 1N aqueous hydrochloric acid solution, water
  2. dry with materiala saturated aqueous sodium chloride solution, dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-f8384c6d59904263b5cd4836c7fa9797
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07807674B2

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