2-Nitropropane → HCID 67509137, compound

HRID 1770756Notes

Reaction equation

HRID 1770756 reaction equation
CN(C)C(N(C)C)=N.[CH2:9]([O:16][CH2:17][CH:18]=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:20]([CH:23]([CH3:25])[CH3:24])([O-:22])=[O:21]>C1COCC1>[CH2:9]([O:16][CH2:17][CH:18]([OH:19])[C:23]([CH3:25])([N+:20]([O-:22])=[O:21])[CH3:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 664601,1,3,3-TetramethylguanidineHCID 108989(Phenylmethoxy)acetaldehyde

Product 1

HCID 67509137HCID 67509137, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1,1,3,3-Tetramethylguanidine (620 μL, 5 mmol) was added slowly to a cold, 0° C., stirring solution of benzyloxy acetaldehyde (4.6 g, 31 mmol) and 2-nitropropane (30 mL, 333 mmol) in 100 mL of anhydrous THF. The reaction was stirred at 0° C. for ten minutes then allowed to warm to room temperature and stirred for 18 hours. The reaction was concentrated under reduced pressure and the product purified by column chromatography (5 to 50% ethyl acetate in hexanes) to give the title compound as a clear liquid (6.4 g, 27 mmol, 84%). 1H NMR (CDCl3, 400 MHz) δ 1.58 (s, 3H), 1.63 (s, 2H), 2.87-2.89 (d, J=5.0 Hz, 1H), 3.48-3.53 (dd, 6.8, 9.8 Hz, 1H), 3.60-3.63 (dd, J=4.5, 9.8 Hz, 1H) 4.29-4.33 (m, 1H), 4.57 (s, 2H), 7.32-7.39 (m, 5H). LRMS (ESI/APCI) m/z 238 [M−H+].

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customthe product purified by column chromatography (5 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4b8c664a0bb44ca688d7173b454c52a1
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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