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

HRID 1624258Notes

Reaction equation

HRID 1624258 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-15f683a80b1e41bcb6faef1f4f7ef878
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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