Methyl morpholine oxide → (2E)-3-methyl-2-heptenal

HRID 1976706Notes

Reaction equation

HRID 1976706 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH2:8][CH3:9])=[CH:3]\[CH2:4][OH:5].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1]/[C:2](/[CH2:6][CH2:7][CH2:8][CH3:9])=[CH:3]\[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 10725372(E)-3-Methyl-hept-2-en-1-ol

Product 1

HCID 10630490(2E)-3-methyl-2-heptenalYield 98%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension solution of alcohol 13b (739 mg, 5.7 mmol), 4 Å molecular sieves (2.9 g, activated), and NMO (1.33 g, 11.4 mmol) in CH2Cl2 (12 mL) at 0° C., was added TPAP (120 mg,0.34 mmol) in one-portion. The resulting dark reaction mixture was allowed to stir at 0° C. for 30 min, before being diluted with CH2Cl2 (20 mL), and then filtered through a short pad of silica gel. The filtrate was concentrated in vacuo to afford aldehyde 14c (704 mg, 98% yield) as a colorless oil. The aldehyde is sufficiently pure for immediate use without further purification:

Workup

  1. customThe resulting dark reaction mixture
  2. filtrationfiltered through a short pad of silica gel
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7a8b193454b94d6f885dbd2e5648925c
Source dataset
uspto-grants-2001_05
Patent number
US06228882B1

Reaction notes

Loading…