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Dimethyl Sulfide → (Z)-(3S,5S)-1-(2-chloroethylidene)-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylenecyclohexane

HRID 581622
ノート
印刷プレビュー

反応式

HRID 581622 の反応式
ClN1C(=O)CCC1=O.CSC.[C:12]([Si:16]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[O:17][C@H:18]1[CH2:23][C@@H:22]([O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21]/[C:20](=[CH:42]/CO)/[C:19]1=[CH2:45])([CH3:15])([CH3:14])[CH3:13].[CH2:58]([Cl:60])Cl>>[Cl:60][CH2:58]/[CH:42]=[C:20]1\[C:19](=[CH2:45])[C@@H:18]([O:17][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:23][C@@H:22]([O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:21]\1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 1068Dimethyl SulfideHCID 6344Dichloromethane2 回HCID 31398ChlorosuccinimideHCID 86754184(Z)-(3S,5S)-2-[3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohexylidene]-ethanol

生成物 1

HCID 86754183(Z)-(3S,5S)-1-(2-chloroethylidene)-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylenecyclohexane

実験手順

1.31 g (9.81 mmol) of N-chloro-succinimide in 34 ml of abs. CH2Cl2 was treated at -10° with 749 μl (10.2 mmol) of dimethyl sulfide. 15 Minutes later, 2.95 g (4.559 mmol) of (Z)-(3S,5S)-2-[3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohexylidene]-ethanol, dissolved in 10 ml of CH2Cl2, was slowly added to the resultant white suspension at the same temperature and then stirred for additional 30 minutes at RT. The reaction mixture was then poured onto crushed ice, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97.5/2.5) yielded 2.76 g of (Z)-(3S,5S)-1-(2-chloro-ethylidene)-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohexane as yellowish foam.

後処理

  1. additionwas slowly added to the resultant white suspension at the same temperature
  2. additionThe reaction mixture was then poured
  3. customonto crushed ice
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-b3f33cfb10244b928558bfeec5d6d31e
出典データセット
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05919986

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート