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Sodium Thiosulfate → 3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehyde

HRID 348736
ノート
印刷プレビュー

反応式

HRID 348736 の反応式
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH2:22][OH:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH:22]=[O:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 230791693-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-ol

生成物 1

HCID 230791943-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehyde収率 83.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

The compound (1.18 g) obtained in Example 121-6 was dissolved in anhydrous dichloromethane (25 ml) and added with Dess-Martin periodinane (1.82 g), followed by stirring at room temperature for 2 hours. After completion of the reaction, a sodium thiosulfate aqueous solution and a saturated aqueous sodium bicarbonate solution were added to the solution, and the whole was stirred. Then, the solution was extracted with chloroform and the extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution and a saturated sodium bicarbonate aqueous solution. Then, the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (981 mg) as a white solid.

後処理

  1. customAfter completion of the reaction
  2. stirringthe whole was stirred
  3. extractionThen, the solution was extracted with chloroform
  4. washthe extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution
  5. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-70af4eed4917440d9197a820f48ee9cb
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176227B2

反応ノート

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