Isopropyl iodide → HCID 22420759, compound

HRID 1440961Notes

Reaction equation

HRID 1440961 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC(C)C)(C)C.[F:13][CH:14]([C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16].IC(C)C>CCCCCC.O1CCCC1.C(OCC)C.CN(C)P(=O)(N(C)C)N(C)C>[CH3:27][O:26][C:24]1[CH:23]=[C:22]([O:28][CH3:29])[N:21]=[C:20]([C:14]([F:13])([CH:2]([CH3:3])[CH3:1])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:25]=1

Participants

9

Reactant 4

HCID 6362Isopropyl iodideHCID 7912DiisopropylamineHCID 22420763HCID 22420763, compoundHCID 178418339Butyllithium

Product 1

HCID 22420759HCID 22420759, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-60 °C

Procedure

Butyllithium (12.8ml of a 1.6M solution in hexane) was added to di-isopropylamine (3.05ml) in dry tetrahydrofuran (120ml) under nitrogen at a temperature of -78° C. and the mixture was stirred for 30 minutes. The product of Example 1 (3.4g) in dry tetrahydrofuran (20ml) was then added at a temperature of -65° C., and the mixture was stirred for 1 hour, during which the temperature rose to -30° C. After cooling to -60° C., 3.18 g of hexamethylphosphoric triamide were added, and the mixture was stirred for 15 minutes. Then 2-iodopropane (3.4 g) was added, and the mixture was stirred at room temperature for 72 hours, after which it was diluted with 100ml diethyl ether, and washed with a saturated ammonium chloride and sodium chloride solution. The aqueous phase was extracted with diethyl ether, and the organic layer was dried over magnesium sulfate and evaporated. The yellow oil obtained was finally chromatographed on silica gel using hexane/ethyl acetate (0-5% ethyl acetate) to give 1.46 g of the desired product, refractive index at 20° C. =1.4756.

Workup

  1. stirringthe mixture was stirred for 1 hour, during which the temperature
  2. customrose to -30° C
  3. stirringthe mixture was stirred for 15 minutes
  4. stirringthe mixture was stirred at room temperature for 72 hours
  5. washwashed with a saturated ammonium chloride and sodium chloride solution
  6. extractionThe aqueous phase was extracted with diethyl ether
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. customevaporated
  9. customThe yellow oil obtained
  10. customwas finally chromatographed on silica gel

Sources & evidence

ORD record
ord-8332b1104fba433888f67f0f59199136
Source dataset
uspto-grants-1996_03
Patent number
US05502028

Reaction notes

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