Pyripropanol → 3-(Pyridin-2-YL)propanal

HRID 899614Notes

Reaction equation

HRID 899614 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][OH:10].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH:9]=[O:10]

Participants

5

Reactant 2

HCID 72922PyripropanolHCID 82029Methyl morpholine oxide

Product 1

HCID 114007983-(Pyridin-2-YL)propanalYield 11.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-pyridinepropanol (1.00 g, 7.29 mmol), NMO (1.281 g, 10.94 mmol) and 3 Å molecular sieves (3.645 g) in CH2Cl2 (37 mL) was added TPAP (256 mg, 0.73 mmol). The resulting black mixture was stirred at room temperature overnight. The mixture was concentrated and filtered through a silica gel plug. Purification by column chromatography on silica gel (EtOAc, 100%) afforded the desired aldehyde (111 mg, 11%) as a yellow syrup. 1H NMR (CDCl3) δ 2.90-2.95 (m, 2H), 3.11 (t, 2H, J=7.0 Hz), 7.09 (dd, 1H, J=7.0, 4.8 Hz), 7.17 (d, 1H, J=7.8 Hz), 7.54-7.63 (m, 1H), 8.48 (d, 1H, J=4.2 Hz), 9.86 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationfiltered through a silica gel plug
  3. customPurification by column chromatography on silica gel (EtOAc, 100%)

Sources & evidence

ORD record
ord-8bb75e15931d4184bfdaf4f1e46ebe77
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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