Isopropyl iodide → HCID 54028132, compound

HRID 2286789Notes

Reaction equation

HRID 2286789 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].C([Li])CCC.[C:13]1([C:19]([CH3:25])=[CH:20][CH2:21][C:22]([OH:24])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(I)(C)C>C1COCC1.CCCCCC.O>[CH:1]([CH:21]([CH:20]=[C:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:25])[C:22]([OH:24])=[O:23])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6362Isopropyl iodideHCID 7912DiisopropylamineHCID 583144HCID 583144, compoundHCID 178418339Butyllithium

Product 1

HCID 54028132HCID 54028132, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 3.2 ml (23 mmole) diisopropylamine in 15 ml THF at 0° under nitrogen is added 14.4 ml (23 mmole) 1.6 M n-butyllithium. The reaction is warmed to RT over 2 hr and cooled to 0°, and 2.0 g (11.4 mmole) 4-phenyl-3-pentenoic acid in several ml of THF is added. After 1.5 hr at about 10°, 1.16 ml (11.6 mmole) isopropyl iodide is added and the reaction stirred about 60 hours. The reaction is poured into water and hexane. The aqueous phase is acidified and extracted with ether. The ether extracts are washed to neutrality, dried over calcium sulfate and solvent removed under vacuum to give 2-isopropyl-4-phenyl-3-pentenoic acid.

Workup

  1. temperaturecooled to 0°
  2. extractionextracted with ether
  3. washThe ether extracts are washed to neutrality
  4. dry with materialdried over calcium sulfate and solvent
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-cdbed0d556cd4762b1d9a05fb8902bcb
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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