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

HRID 348736
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HRID 348736 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 230791693-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-ol

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-70af4eed4917440d9197a820f48ee9cb
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176227B2

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