Ethanol → 4-[(3-Ethyloxetan-3-yl)methoxy]aniline

HRID 1429232Notes

Reaction equation

HRID 1429232 reaction equation
[CH2:1]([C:3]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:6][O:5][CH2:4]1)[CH3:2].C1COCC1.CCO.[Cl-].[NH4+]>[Fe].O>[CH2:1]([C:3]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:4][O:5][CH2:6]1)[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 666297443-Ethyl-3-[(4-nitrophenoxy)methyl]oxetane

Product 1

HCID 666302764-[(3-Ethyloxetan-3-yl)methoxy]anilineYield 98.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-ethyl-3-((4-nitrophenoxy)methyl)oxetane (8.28 g, 34.9 mmol) in a 3:3:1 mixture of THF:EtOH:water (140 mL) at room temperature was added ammonium chloride (2.80 g, 52.3 mmol) followed by iron powder (9.74 g, 174 mmol). The mixture was heated to 90° C. for 1 hour, then it was filtered hot through diatomaceous earth with a THF wash to complete the transfer. The filtrate was concentrated under reduced pressure, and the residue was taken up in ethyl acetate then washed with brine, dried (Na2SO4), and concentrated to provide the title compound (7.12 g, 98% yield) without further purification.

Workup

  1. filtrationit was filtered hot through diatomaceous earth with a THF
  2. washwash
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthen washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-199de2aa7e184ab586223eb9495dc499
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…