Hydrochloric Acid → 4-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone

HRID 732855

반응식

HRID 732855 반응식
[CH3:1][C:2]1[CH:7](/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11])[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=1.[SH:15][CH2:16][CH2:17][CH2:18][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].C1CCN2C(=NCCC2)CC1.Cl>>[CH3:21][O:20][Si:19]([O:22][CH3:23])([O:24][CH3:25])[CH2:18][CH2:17][CH2:16][S:15][CH:8]([CH:7]1[C:6]([CH3:14])([CH3:13])[CH2:5][CH2:4][CH:3]=[C:2]1[CH3:1])[CH2:9][C:10](=[O:11])[CH3:12]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5282108Alpha-Ionone

생성물 1

HCID 688154354-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone수율 71.3%

실험 절차

To a stirred solution of α-ionone (1.92 g, 10.0 mmol) and 3-mercaptopropyl-trimethoxysilane (1.96 g, 10.0 mmol) at 12° C. was rapidly added DBU (0.14 ml, 152 mg, 1.0 mmol). The temperature rose to 19° C. and the solution turned orange. After 135 minutes at 20° C, the reaction mixture was poured onto a cold stirred 5% aqueous HCl solution and extracted twice with Et2O. The organic phases were washed (H2O, saturated aqueous NaHCO3 and brine), dried (Na2SO4), filtered and concentrated. The crude extract was dried for 1 hour at 65-70° C./0.01 Torr to give 2.77 g of the title thioether (71%).

후처리

  1. customat 12° C.
  2. customrose to 19° C.
  3. additionthe reaction mixture was poured onto
  4. extractionextracted twice with Et2O
  5. washThe organic phases were washed (H2O, saturated aqueous NaHCO3 and brine)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. extractionThe crude extract
  10. customwas dried for 1 hour at 65-70° C./0.01 Torr

출처 및 근거

ORD 기록
ord-c9d5ac5521e349c7a2a62136574918c6
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589055B2

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