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

HRID 347415ノート

反応式

HRID 347415 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ad429361b394bd0b98ea62002fc7b55
出典データセット
uspto-grants-2007_02
特許番号
US07173151B2

反応ノート

読み込み中…