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Toluene → 2-Hydroxyethyl-1-(4-methylphenyl)sulfonyl-1H-indole

HRID 54846
ノート
印刷プレビュー

反応式

HRID 54846 の反応式
C(OC([C:6]1[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])C2[C:13]([CH:14]=1)=CC=CC=2)=O)C.[OH-:25].[Na+].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[OH:25][CH2:13][CH2:14][C:6]1[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:32]2[C:27]([CH:33]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 14783456Nod-IN-1

生成物 1

HCID 162030902-Hydroxyethyl-1-(4-methylphenyl)sulfonyl-1H-indole収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To stirred solution of Red-A1 (sodium dihydro-bis(2-methoxyethoxy)aluminate≈70% in toluene) (30 mL) in dry THF (100 mL) cooled at 5° C. and under nitrogen was added dropwise and at this temperature a solution of compound of step 1 (26,8 g, 78 mmol) in dry THF (75 mL). After stirring one hour at 5° C. and then one hour at room temperature the mixture was cooled at 10° C. and treated dropwise with 2N NaOH, to effect hydrolysis of the intermediate complex. The organic phase was separated and the solvent in vacuo evaporated. The residue was solved in ethyl ether, the solution washed with water, dried over MgSO4 and evaporated to give the required alcohol (23.3 g, 98%) as a yellow oil; IR (film) 3500, 1597 cm-1.

後処理

  1. temperatureone hour at room temperature the mixture was cooled at 10° C.
  2. customhydrolysis of the intermediate complex
  3. customThe organic phase was separated
  4. customthe solvent in vacuo evaporated
  5. washthe solution washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated

出典と根拠

ORDレコード
ord-3ea63432e65e4a2ba31124427b761214
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05622983

反応ノート

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