Isobutylene → HCID 58993764, compound

HRID 2408509Notes

Reaction equation

HRID 2408509 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:18][C:19](=[CH2:21])[CH3:20]>C1COCC1.S(=O)(=O)(O)O>[C:19]([O:16][C:15]([C:10]1([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:17])([CH3:21])([CH3:20])[CH3:18]

Participants

5

Reactant 2

HCID 8255IsobutyleneHCID 28530781-(4-nitrophenyl)cyclopentane-1-carboxylic Acid

Product 1

HCID 58993764HCID 58993764, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-nitro-phenyl)-cyclopentanecarboxylic acid (as prepared in the previous step) in THF at −78° C. in a pressure bottle is treated with 2 drops of concentrated sulfuric acid, and isobutylene gas is condensed into the mixture. The mixture is stirred 24 h at RT, cooled to −78° C. and quenched with satd aq NaHCO3. The mixture is warmed to RT and extracted with EtOAc. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography with an appropriate solvent to afford the title compound.

Workup

  1. customcondensed into the mixture
  2. temperaturecooled to −78° C.
  3. customquenched with satd aq NaHCO3
  4. temperatureThe mixture is warmed to RT
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer is dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography with an appropriate solvent

Sources & evidence

ORD record
ord-a9a0499002a248dba34efed7d7c4a447
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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