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

HRID 732855

反応式

HRID 732855 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c9d5ac5521e349c7a2a62136574918c6
出典データセット
uspto-grants-2009_09
特許番号
US07589055B2

関連ノート

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