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Ethyl vinyl ether → 15-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile

HRID 892641
ノート
印刷プレビュー

反応式

HRID 892641 の反応式
[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:15]([OH:18])[C:16]#[N:17].[CH:25]([O:27][CH2:28][CH3:29])=[CH2:26].C(=O)([O-])O.[Na+].CCCCCC.CCOCC>ClCCl>[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:20])[CH3:21])[CH:15]([O:18][CH:25]([O:27][CH2:28][CH3:29])[CH3:26])[C:16]#[N:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 21584099Diethylether hexaneHCID 5450637515-Chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile

生成物 1

HCID 5373709415-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile収率 87.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 15-chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile (204 mg, 0.56 mmol) prepared in Reference Example 6 and ethyl vinyl ether (100 μl, 0.96 mmol) in dichloromethane (5 ml) is added a very small amount of paratoluenesulfonic acid while stirring under nitrogen atmosphere on an ice-water bath. After 10 minutes, to the mixture are added a saturated aqueous sodium hydrogencarbonate solution (15 ml) and n-hexane/ether (1:1) solution (20 ml) and the organic layer is separated. The aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times. The organic layers are combined and dried over anhydrous sodium sulfate and the solvent is removed by distillation under reduced pressure. The resulting residue is purified by silca gel column chromatography (n-hexane/ethyl acetate =20:1) to give 15-chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile (207 mg, 85%).

後処理

  1. additionis added a very small amount of paratoluenesulfonic acid
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is removed by distillation under reduced pressure
  6. customThe resulting residue is purified by silca gel column chromatography (n-hexane/ethyl acetate =20:1)

出典と根拠

ORDレコード
ord-f1d50ab4d198432f890e491bff12e39f
出典データセット
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05118827

反応ノート

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