1-Butanol → HCID 178450850, compound

HRID 409220Notes

Reaction equation

HRID 409220 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:26])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:24])[CH:12]=2)[C:7]1=[O:25].Cl.CCOC(C)=O.[CH2:34](O)[CH2:35][CH2:36]C>>[CH2:2]([O:3][C:4]([C:5]1[N:6]=[C:7]([OH:25])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([O:16][C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:24])=[CH:10][CH:9]=2)=[O:26])[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 5

HCID 2631-Butanol2×HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 66713069HCID 66713069, compound

Product 1

HCID 178450850HCID 178450850, compoundYield 43%

Conditions

Temperature
70 °C

Procedure

Sodium (1 eq) was dissolved in n-butanol (1.6 mL/mmol) with stirring at 70° C. Subsequently, the temperature was raised to 95° C. before a solution of [5-(2,6-Dimethyl-phenoxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid methyl ester (0.5 eq) in hot n-butanol (2.3 mL/mmol) was added in one portion with stirring. Stirring was continued at 95° C. for 3 h before the mixture was concentrated in vacuo. To the residue was added 2 N hydrochloric acid (1.3 eq) and EtOAc (ca. 4-fold volume) and the mixture was stirred vigorously for 45 min. Subsequently, the solid component was sucked off, washed with water and dried in vacuo before it was suspended in EtOAc (ca. 20 mL/g) and the mixture was refluxed with stirring for 2 h. After cooling to ambient temperature the solid component was sucked off, washed with EtOAc and dried in vacuo to give the title compound as an off-white solid (yield: 43%); MS-(+)-ion: M+1=382.5

Workup

  1. additionwas added in one portion
  2. stirringwith stirring
  3. stirringStirring
  4. concentrationwas concentrated in vacuo
  5. stirringthe mixture was stirred vigorously for 45 min
  6. washwashed with water
  7. customdried in vacuo before it
  8. temperaturethe mixture was refluxed
  9. stirringwith stirring for 2 h
  10. temperatureAfter cooling to ambient temperature the solid component
  11. washwashed with EtOAc
  12. customdried in vacuo

Sources & evidence

ORD record
ord-e74dfd436cff451ab08a2e88f0bad138
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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