2-Bromoethanol → 2-{2-[2-(4-Vinylbenzylthio)ethoxy]ethylthio}ethanol

HRID 248609

반응식

HRID 248609 반응식
[OH-].[K+].[SH:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][SH:9].Br[CH2:11][CH2:12][OH:13].[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1)=[CH2:15]>C(O)C>[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][S:9][CH2:11][CH2:12][OH:13])=[CH:18][CH:17]=1)=[CH2:15]

참가 물질

6

반응물 4

HCID 108982-BromoethanolHCID 14797Potassium Hydroxide2회HCID 74126p-Vinylbenzyl chlorideHCID 750732,2'-Oxybisethanethiol

생성물 1

HCID 191054422-{2-[2-(4-Vinylbenzylthio)ethoxy]ethylthio}ethanol수율 43.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromatography on the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's).

후처리

  1. stirringstirring
  2. waitwas continued at ambient temperature for 30 minutes
  3. stirringagain stirring
  4. waitwas continued at ambient temperature for 30 minutes
  5. stirringstirred at room temperature for 16 hours
  6. filtrationThe next day the reaction was filtered
  7. customthe solvent removed on a rotary evaporator
  8. additionTo the residue was added dichloromethane (1.2 liter)
  9. washthe mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml)
  10. dry with materialthen dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed in a rotary evaporator
  13. additionTo the residue was added diethyl ether (350 ml) and hexane (200 ml)
  14. temperaturethe mixture was cooled in the freezer
  15. filtrationfiltered

출처 및 근거

ORD 기록
ord-75f782c23277485b8f5164ad6538ce91
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210289

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