Hydrochloric Acid → 2,3-Diphenyl-5-methylamino-2,5-dihydrofuran hydrochloride

HRID 1789096노트

반응식

HRID 1789096 반응식
[C:1]1([CH:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]([NH:18][CH3:19])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[H-].[Na+].CN=CCP(=O)(OCC)OCC.[ClH:50]>O1CCCC1.C(OCC)(=O)C.C(OCC)C.O>[ClH:50].[C:1]1([CH:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]([NH:18][CH3:19])[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 8400BenzoinHCID 24758Sodium hydrideHCID 201336832,3-Diphenyl-5-methylamino-2,5-dihydrofuranHCID 20133694Diethyl 2-methyliminoethylphosphonate

생성물 1

HCID 201337222,3-Diphenyl-5-methylamino-2,5-dihydrofuran hydrochloride

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

2,3-Diphenyl-5-methylamino-2,5-dihydrofuran can be prepared as follows: benzoin (29.7 g) dissolved in tetrahydrofuran (400 cc) is added to a suspension of sodium hydride (3.4 g) in tetrahydrofuran (50 cc) kept under a nitrogen atmosphere at a temperature in the region of 0° C., and the reaction mixture is stirred for 30 minutes while the temperature is allowed to return to 20° C. Diethyl 2-methyliminoethylphosphonate (27 g) in tetrahydrofuran (270 cc) is then added. The reaction mixture is then heated to reflux for 1 hour and then cooled to a temperature in the region of 20° C. Water (1 liter) is then added and the mixture is extracted twice with ethyl acetate (200 cc in total). The organic phase is washed with water (2×100 cc) and then dried over magnesium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue is washed with ethyl ether (100 cc) and then filtered. The filtrate is evaporated to dryness under reduced pressure (2.7 kPa) at 40° C. to give an oil which is purified by "flash" chromatography [eluent: ethyl acetate]. After fractions 8 and 19 have been evaporated to dryness under reduced pressure (2.7 kPa) at 40° C., an orange oil is obtained which is dissolved in a mixture (20 cc) of ethyl acetate and ethyl ether (50/50 by volume). A 5.7N solution (3.9 cc) of hydrochloric acid gas in ethyl ether is added to the solution. The solid obtained is separated off by filtration and then recrystallised from isopropanol (120 cc). In this way 2,3-diphenyl-5-methylamino-2,5-dihydrofuran hydrochloride (2.8 g) is obtained in the form of a white solid melting at 190° C.

후처리

  1. customkept under a nitrogen atmosphere at a temperature in the region of 0° C.
  2. customto return to 20° C
  3. temperatureThe reaction mixture is then heated
  4. temperatureto reflux for 1 hour
  5. extractionthe mixture is extracted twice with ethyl acetate (200 cc in total)
  6. washThe organic phase is washed with water (2×100 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure (2.7 kPa) at 40° C
  10. washThe residue is washed with ethyl ether (100 cc)
  11. filtrationfiltered
  12. customThe filtrate is evaporated to dryness under reduced pressure (2.7 kPa) at 40° C.
  13. customto give an oil which
  14. customis purified by "flash" chromatography [eluent: ethyl acetate]
  15. customAfter fractions 8 and 19 have been evaporated to dryness under reduced pressure (2.7 kPa) at 40° C.
  16. customan orange oil is obtained which
  17. customThe solid obtained
  18. customis separated off by filtration
  19. customrecrystallised from isopropanol (120 cc)

출처 및 근거

ORD 기록
ord-475f9554de1148c0944b4557eb4b3965
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04686309

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