Nitroethane → HCID 11356253, compound

HRID 1366963Notes

Reaction equation

HRID 1366963 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[C:6]1([CH2:12][CH2:13][CH:14]=[O:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N12CCCN=C1CCCCC2>C1COCC1.C(OCC)C.O>[N+:1]([CH:4]([CH3:5])[CH:14]([OH:15])[CH2:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 6587NitroethaneHCID 7707BenzenepropanalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 11356253HCID 11356253, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Following the procedure of One et al, J. Heterocyclic Chem., 1994, 31, 707-710, which is incorporated by reference, nitroethane (10 mL, 139.2 mmol, 96%) and 3-phenylpropionaldehyde (18.49 mL, 139.9 mmol) were dissolved in THF (70 mL, 2 M). After cooling to −10° C. in a brine bath, 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) (1.46 mL, 9.74 mmol) was added, and allowed to stir until complete by HPLC (75 min). The reaction was diluted with diethyl ether and H2O, and then the organic was removed and washed with saturated aqueous NaHCO3 and brine. The aqueous layers were back-extracted with diethyl ether, and the combined organics were dried with Na2SO4, filtered, and concentrated to provide 179, which was used without further purification in the next step. HPLC: 9.68 min. (Note: The retention time for the starting materials follow: nitroethane: 6.49 min.; 3-phenylpropionaldehyde: 9.45 min).

Workup

  1. customthe organic was removed
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. extractionThe aqueous layers were back-extracted with diethyl ether
  4. dry with materialthe combined organics were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3318900ed81e4d84bd84e6a671db8272
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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