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

HRID 732854

반응식

HRID 732854 반응식
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]([CH3:14])=[O:13].[SH:15][CH2:16][CH2:17][CH2:18][Si:19]([O:24][CH3:25])([O:22][CH3:23])[O:20][CH3:21].Cl>C1CCN2C(=NCCC2)CC1>[CH3:21][O:20][Si:19]([O:22][CH3:23])([O:24][CH3:25])[CH2:18][CH2:17][CH2:16][S:15][CH:10]([C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[CH2:11][C:12](=[O:13])[CH3:14]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 638014I2-Ionone

생성물 1

HCID 688178914-{[3-(Trimethoxysilyl)propyl]thio}-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone수율 88.9%

시약·촉매·용매 1

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매

실험 절차

To a well-stirred mixture of β-ionone (10.00 g, 52.1 mmol) and DBU (79 mg, 0.52 mmol (1 mol-%)) was rapidly added 3-mercaptopropyltrimethoxysilane (10.21 g, 52.1 mmol) at 25-30° C. After 72 hours, 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 18.00 g of the title thioether containing approximativaly 10% of β-ionone. Yield: 80%.

후처리

  1. customat 25-30° C
  2. additionthe reaction mixture was poured onto
  3. extractionextracted twice with Et2O
  4. washThe organic phases were washed (H2O, saturated aqueous NaHCO3 and brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionThe crude extract
  9. customwas dried for 1 hour at 65-70° C./0.01 Torr

출처 및 근거

ORD 기록
ord-f419cbac44c6454b93d26078fa5db95a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589055B2

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