Sodium Hydroxide → 4,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene

HRID 572905

반응식

HRID 572905 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:14])[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](=[O:13])[C:2]1=2.[OH-].[Na+].C1(C)C=CC(S(O[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=O)=O)=CC=1>[Zn].C(O)C>[CH2:5]([O:14][C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([O:13][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH3:27])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH2:4][CH2:3][CH2:2][CH2:12][CH2:11][CH2:7][CH3:6]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 599296n-Octyl p-Toluenesulfonate

생성물 1

HCID 582808994,8-Bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene수율 62%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 702Ethanol용매

실험 절차

1.0 g (4.5 mmol) of benzo[1,2-b:4,5-b′]dithiophene-4,8-dione was mixed with 0.65 g (10 mmol) of zinc dust in a flask. Then, 4 ml of ethanol and 15 ml of 20% NaOH was added and the mixture was refluxed for 1 h. 4.3 mL octyl p-toluenesulfonate was added in portions with stirring until the color changed to red. The resulting precipitate was filtered, the filtrate was diluted with 100 mL water and extracted with 100 mL chloroform. The organic extraction was dried with anhydrous sodium sulfate and evaporated in vacuo. Column chromatography on silica gel using dichloromethane and hexanes mixed solvents yielded the pure title compound as a white solid (1.24 g, 62%). 1HNMR (CDCl3): δ0.88-0.91 (6H, t, J=7 Hz), 1.31-1.38 (16H, m), 1.54-1.58 (4H, m), 1.84-1.89 (4H, m), 4.26-4.29 (4H, J=7 Hz), 7.36-7.37 (2H, d, J=6 Hz), 7.47-7.48 (2H, d, J=6 Hz).

후처리

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe resulting precipitate was filtered
  3. additionthe filtrate was diluted with 100 mL water
  4. extractionextracted with 100 mL chloroform
  5. extractionThe organic extraction
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-ce4e26891ada4a07a16e88b0ca418783
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029499B2

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