Water → 3-Ethyl-3-[(4-nitrophenoxy)methyl]oxetane

HRID 1429231Notes

Reaction equation

HRID 1429231 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17]([C:19]1([CH2:23][OH:24])[CH2:22][O:21][CH2:20]1)[CH3:18].O>CS(C)=O>[CH2:17]([C:19]1([CH2:23][O:24][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:22][O:21][CH2:20]1)[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 76444Oxt-101

Product 1

HCID 666297443-Ethyl-3-[(4-nitrophenoxy)methyl]oxetaneYield 98.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluoronitrobenzene (3.76 mL, 35.4 mmol) in DMSO (35 mL) at room temperature was added cesium carbonate (7.09 mL, 89.0 mmol) followed by 3-ethyl-3-oxetanemethanol (4.48 mL, 42.5 mmol). The mixture was heated to 70° C. for 2 hours. After cooling water was added and the resulting precipitate was filtered, washed with water, and dried in a vacuum oven to provide the title compound (8.28 g, 98% yield).

Workup

  1. additionwas added
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e76bfd0d0a7249e8b769df34062225fa
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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