Hydrochloric Acid → Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate

HRID 2217096

반응식

HRID 2217096 반응식
[CH3:1][Si:2]([CH3:12])([CH3:11])[C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.CC(C)([O-])C.[K+].Br[C:20]1[O:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:21]=1.Cl>C1COCC1.O>[CH3:10][C:6]1[CH:5]=[CH:4][C:3]([Si:2]([CH3:11])([CH3:12])[CH3:1])=[CH:8][C:7]=1[O:9][C:20]1[O:24][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 599633Methyl 5-bromofuran-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 597674632-Methyl-5-(trimethylsilyl)phenol2회

생성물 1

HCID 53397016Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate수율 57%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-trimethylsilyl-2-methylphenol (Intermediate 3; 653 mg, 3.6 mmol) in THF was added potassium tert-butoxide (407 mg, 3.6 mmol) and the reaction heated at reflux for 1.5 hours. The resulting solution was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in dimethyl sulphoxide (10 mL), treated with methyl 5-bromo-2-furoate (632 mg, 3.1 mmol) and heated at 85° C. for 18 hours. The dark brown mixture was allowed to cool to room temperature, diluted with water (10 mL) and then acidified by the addition of hydrochloric acid (1 M). The mixture was extracted with diethyl ether (3×30 mL) and the combined organic extracts were dried (magnesium sulphate), concentrated under reduced pressure and purified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether) to give the title compound as a colourless oil (534 mg, 57%). Rf=0.21 (9:1 light petroleum-diethyl ether). LCMS Rt=4.9 mins, m/z=305 (MH+).

후처리

  1. temperaturethe reaction heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated under reduced pressure
  4. temperatureheated at 85° C. for 18 hours
  5. temperatureto cool to room temperature
  6. extractionThe mixture was extracted with diethyl ether (3×30 mL)
  7. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  8. concentrationconcentrated under reduced pressure
  9. custompurified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether)

출처 및 근거

ORD 기록
ord-c4886fd4254b44baa3e2eac68dba9c4d
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407649B2

연결된 노트

불러오는 중…