Sodium Thiosulfate → (1R,2R)-2-phenylcyclopropane-1-carbaldehyde

HRID 1602571노트

반응식

HRID 1602571 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:6]1([C@@H:4]2[CH2:5][C@H:3]2[CH:2]=[O:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 1561175(2-phenylcyclopropyl)methanol

생성물 1

HCID 12323031(1R,2R)-2-phenylcyclopropane-1-carbaldehyde수율 50.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

104 mg of the alcohol was dissolved in 5 ml of chloroform and stirred with 445 mg of the Dess-Martin reagent (periodinane) at room temperature for 30 minutes. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 52 mg of the title compound as a colorless oily substance.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

출처 및 근거

ORD 기록
ord-ad075589ec584c1a8818aa1c1416644c
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981573

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