Water → HCID 67226454, compound

HRID 629665Notes

Reaction equation

HRID 629665 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.F[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:13]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[O:22]([C:14]1[CH:13]=[C:12]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 67144536Benzoic acid, 4-fluoro-2-phenoxy-, methyl ester

Product 1

HCID 67226454HCID 67226454, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,4-dioxa-8-azaspiro[4.5]decane (1.18 g), methyl 4-fluoro-2-phenoxybenzoate (1.85 g), and K2CO3 (1.14 g) was stirred at 125° C. in dimethylsulfoxide (25 mL) for 24 hours. The mixture was cooled, poured into 300 mL water, extracted three times with ether, and the ether extracts were combined, rinsed three times with water, and brine, and concentrated. The residue was chromatographed on silica gel using 10-30% ethyl acetate in hexanes as eluent to give the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted three times with ether
  3. washrinsed three times with water, and brine
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel using 10-30% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-235029d9a4654ca88ba371874f9f7102
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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