Water → Tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate

HRID 347415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347415
C(OP([CH:9]([CH2:17][CH3:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.C([Li])CCC.[O:24]([C@@H:42]1[CH2:47][CH2:46][CH2:45][C@H:44]([CH2:48][CH:49]=O)[CH2:43]1)[Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>O1CCCC1.CCCCCC>[Si:25]([O:24][C@@H:42]1[CH2:47][CH2:46][CH2:45][C@H:44]([CH2:48][CH:49]=[C:9]([CH2:17][CH3:18])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:43]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 21082801Tert-butyl 2-(diethoxyphosphoryl)butyrateHCID 86594888[cis-3-(Tert-butyl-diphenylsilanyloxy)cyclohexyl]acetaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 69494093Tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

6.43 g of tert-butyl 2-(diethoxyphosphoryl)butyrate are dissolved in 90 ml of tetrahydrofuran, and 7.32 ml of a 2.7 M solution of n-butyllithium in n-hexane are added at −20° C. After 1 hour of stirring at −20° C., 4.36 g of [cis-3-(tert-butyl-diphenylsilanoxy)cyclohexyl]acetaldehyde, dissolved in 40 ml of tetrahydrofuran, are added dropwise. The reaction mixture is slowly warmed to room temperature. 50 ml of water are then added, and the mixture is extracted three times with in each case 200 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=30:1. This gives 3.11 g of tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate as an oil. C32H46O3Si (506.81), Rf(n-heptane:ethyl acetate=5:1)=0.73.

Aufarbeitung

  1. additionare added dropwise
  2. temperatureThe reaction mixture is slowly warmed to room temperature
  3. extractionthe mixture is extracted three times with in each case 200 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customthe solvent is then removed under reduced pressure
  6. customThe residue is purified on silica gel using the mobile phase n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-9ad429361b394bd0b98ea62002fc7b55
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173151B2

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