Potassium Carbonate → 8-(2,6-Difluoro-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 1411415Notes

Reaction equation

HRID 1411415 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1F.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[C:3]=1[N:20]1[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 580319788-(2,6-Difluoro-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,2,3-trifluoro-5-nitrobenzene (4.0 mL, 34.3 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (6.59 mL, 51.4 mmol) and potassium carbonate (5.68 g, 41.1 mmol) in DMSO (35 mL) was heated at 100° C. for 3 hours and then cooled to room temperature. The mixture was partitioned between water and EtOAc, and the organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-20% EtOAc in hexanes to give a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture was partitioned between water and EtOAc
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-20% EtOAc in hexanes
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-1b8ceb2dd0644042b3a59ad40408ced0
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Reaction notes

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