Triacetoxyperiodinane → 3-(3-Methoxypropyl)benzaldehyde

HRID 561778노트

반응식

HRID 561778 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH:12]=[O:13]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 66761215[3-(3-Methoxypropyl)phenyl]methanol

생성물 1

HCID 579560643-(3-Methoxypropyl)benzaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a CH2Cl2 solution (0.3 M) of [3-(3-methoxypropyl)phenyl]methanol from the previous step (1 eq.) was added Dess-Martin periodinane (1.2 eq.). The resulting suspension was stirred at RT for 2 h. The reaction was quenched with sat. aq. NaHCO3 and 2 N aq. Na2S2O3. The biphasic mixture was allowed to stir at RT for 20 min, poured into sat. aq. NaHCO3 and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a cloudy oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

후처리

  1. customThe reaction was quenched with sat. aq. NaHCO3 and 2 N aq. Na2S2O3
  2. stirringto stir at RT for 20 min
  3. additionpoured into sat. aq. NaHCO3
  4. extractionextracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a cloudy oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-678d6a5087574539b5298d421ec37b33
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063105B2

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