Isopropyl iodide → HCID 22241954, compound

HRID 2415021Notes

Reaction equation

HRID 2415021 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[Li]CCCC.[CH2:13]([CH:15]([CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:14].IC(C)C.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1>[CH2:13]([C:15]([CH:5]([CH3:6])[CH3:7])([CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:14]

Participants

7

Reactant 5

HCID 6362Isopropyl iodideHCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 4643711HCID 4643711, compoundHCID 178418339Butyllithium

Product 1

HCID 22241954HCID 22241954, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture of 10 mL (72 mmol) of diisopropylamine in 250 mL of tetrahydrofuran (THF) was added 28.6 mL (72 mmol) of BuLi (2.5 molar in cyclohexanes) at −20° C. After 20 minutes stirring, 9.2 g (83% pure) (28.3 mmol) of diethyl 2,3-diethylsuccinate was added at −40° C. and after addition the mixture was stirred for 2 h at room temperature. Then this mixture was cooled to −70° C. and a mixture of 4.3 mL (43 mmol) of 2-iodopropane and 7.4 mL (43 mmol) of hexamethylphosphoramide (HMPA) was added. After addition the cooling was removed and the mixture was stirred for four days. The volatiles were removed and 250 mL of ether was added. The organic layer was washed twice with 100 mL of water. The organic layer was isolated, dried over MgSO4, filtered and concentrated in vacuo yielding an orange oil. This oil was chromatographed over silica with CH2Cl2 yielding 2.3 g (30%) of a 96% pure product. According to gaschromatography (GC) only one isomer was present.

Workup

  1. additionafter addition the mixture
  2. stirringwas stirred for 2 h at room temperature
  3. additionwas added
  4. additionAfter addition the cooling
  5. customwas removed
  6. stirringthe mixture was stirred for four days
  7. customThe volatiles were removed
  8. addition250 mL of ether was added
  9. washThe organic layer was washed twice with 100 mL of water
  10. customThe organic layer was isolated
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customyielding an orange oil
  15. customThis oil was chromatographed over silica with CH2Cl2 yielding 2.3 g (30%) of a 96% pure product

Sources & evidence

ORD record
ord-b34f564b0e604b23aab99c073b64134d
Source dataset
uspto-grants-2004_11
Patent number
US06818583B1

Reaction notes

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