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

HRID 347415노트

반응식

HRID 347415 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ad429361b394bd0b98ea62002fc7b55
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173151B2

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