Iodoethane → HCID 18947544, compound

HRID 1590754Notes

Reaction equation

HRID 1590754 reaction equation
[CH2:1]([Li])[CH2:2]CC.CCCCCC.[Cl:12][C:13](=[CH2:22])[CH2:14][CH:15]([CH2:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17].C(I)C>C1COCC1>[Cl:12][C:13](=[CH2:22])[CH2:14][C:15]([CH2:1][CH3:2])([CH2:20][CH3:21])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8058HexaneHCID 18947556HCID 18947556, compoundHCID 178418339Butyllithium

Product 1

HCID 18947544HCID 18947544, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(0.80 mL, 5.7 mmol) in THF (5 mL) was added a 1.6M solution of butyllithium in hexane (3.4 mL, 5.4 mmol) over a 5 minute period and stirring was continued for an additional 45 min. Then a solution of methyl 4-chloro-2-ethyl-4-pentenoate (800 mg, 5 mmol) from Example 27, Step A, in THF (2 mL) was added and the reaction was stirred at 0° C. for another 30 minutes. Then ethyl iodide (440 μL, 5.5 mmol) was added and the reaction was allowed to proceed at room temperature for 2 hours. The reaction was quenched with NH4OAc buffer (50 mL of 25% w/v) and extracted with EtOAc. The organic layer was separated, dried over MgSO4, filtered and concentrated. The crude product was purified by Kugelrohr distillation (b.p. 120° C. at 0.1 mm Hg) to give the title compound.

Workup

  1. stirringthe reaction was stirred at 0° C. for another 30 minutes
  2. waitto proceed at room temperature for 2 hours
  3. customThe reaction was quenched with NH4OAc buffer (50 mL of 25% w/v)
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationThe crude product was purified by Kugelrohr distillation (b.p. 120° C. at 0.1 mm Hg)

Sources & evidence

ORD record
ord-b29c6e76679a452880abb642ef7310f8
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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