2,4-Pentanediol → 2,4-dimethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

HRID 552871

반응식

HRID 552871 반응식
CO[C:3]1[C:7](OC)=[CH:6][S:5][CH:4]=1.[CH3:10][CH:11]([OH:16])[CH2:12][CH:13]([OH:15])[CH3:14].C(C1C=CC=CC=1S(O)(=O)=O)CCCCCCCCCCC>C(Cl)(Cl)Cl>[CH3:10][CH:11]1[O:16][C:3]2=[CH:4][S:5][CH:6]=[C:7]2[O:15][CH:13]([CH3:14])[CH2:12]1

참가 물질

5

반응물 3

HCID 122622,4-PentanediolHCID 25457Dodecylbenzenesulphonic acid2회HCID 36135013,4-Dimethoxythiophene

생성물 1

HCID 578228902,4-dimethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
100 °C

실험 절차

A three-neck round bottom flask is vacuum dried, fitted with a stir bar, thermometer, and drying tube and maintained under nitrogen. About 500 milliliters (ml) of anhydrous xylene is cannulated into the flask. Two ml of 3,4-dimethoxy thiophene 1 (DMOT) (0.0166 mol), 4.85 ml of 2,4-pentanediol 2 (0.0332), and 0.61 ml of catalyst dodecylbenzene sulfonic acid (DBSA) (0.0025 mol) are added to the flask sequentially with previously degassed disposable syringes through the rubber septa fitted on one of the necks of the flask. The molar proportion between DMOT:diol:DBSA is 1.00:2.00:0.15. The reaction is set to run for five days under stirring at a temperature of around 100° C. The reaction is monitored on a daily basis by gas chromatography-mass spectrometry (GC-MS). After five days, the reaction is cooled to ambient temperature and filtered to remove any solid particulates. The xylene is stripped using a rotary evaporator to result in a green oil. The oil is taken up in a small amount of chloroform and extracted with water three times using sodium chloride to break any emulsion. The chloroform is stripped leaving a green oil. The crude mixture is purified by column chromatography using 70:30 toluene:n-hexane as the eluting solvent. The first fractions contain the product 2,4-dimethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine 3 (aDM-ProDOT) and subsequent fractions contain DMOT 1 starting material. The aDM-ProDOT 3 is isolated as a white solid that is dried under vacuum. The final product was confirmed by GC-MS and 1H-NMR.

후처리

  1. customA three-neck round bottom flask is
  2. customvacuum dried
  3. customfitted with a stir bar
  4. customthermometer, and drying tube
  5. temperaturemaintained under nitrogen
  6. customfitted on one of the necks of the flask
  7. waitAfter five days
  8. temperaturethe reaction is cooled to ambient temperature
  9. filtrationfiltered
  10. customto remove any solid particulates
  11. customa rotary evaporator
  12. customto result in a green oil
  13. extractionextracted with water three times
  14. customThe chloroform is stripped leaving a green oil
  15. customThe crude mixture is purified by column chromatography

출처 및 근거

ORD 기록
ord-94396537dd214c5196b67d7c286bfbd3
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951902B2

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