Triacetoxyperiodinane → 3-(3-Methoxypropyl)benzaldehyde

HRID 561778Notes

Reaction equation

HRID 561778 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 579560643-(3-Methoxypropyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-678d6a5087574539b5298d421ec37b33
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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