Ammonium Chloride → HCID 18800746, compound

HRID 849143Notes

Reaction equation

HRID 849143 reaction equation
[CH2:1]([Li])[CH:2]=[CH2:3].[CH3:5][O:6][C:7](=[O:26])[CH:8]=[CH:9][CH2:10][CH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13](=[O:18])[N:12]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[Cl-].[NH4+]>C1COCC1.[Cu]I>[CH3:24][C:22]([CH3:23])([O:21][C:19]([N:12]1[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH2:17][CH:11]1[CH2:10][CH:9]([CH2:3][CH:2]=[CH2:1])[CH2:8][C:7]([O:6][CH3:5])=[O:26])=[O:20])[CH3:25]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 54226112HCID 54226112, compoundHCID 178506856HCID 178506856, compound

Product 1

HCID 18800746HCID 18800746, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Four equivalents of allyl lithium are added to a stirring suspension of 2 equivalents copper (I) iodide in THF at -50° C. under argon. After the mixtures becomes homogeneous (approx. 20 minutes.), a solution of the title ester of Example 209 (1 equivalent) in THF is added to the cold mixture and stirred below -50° C. for approx. 30 minutes. The mixture is poured into saturated ammonium chloride solution and stirred vigorously for 15 minutes. The mixture is then partitioned between ether and water and the organic layer is washed with water and brine before it is dried (Na2SO4). The mixture is then filtered and stripped of all solvent. The title material is then purified by column chromatography.

Workup

  1. custom(approx. 20 minutes.)
  2. stirringstirred vigorously for 15 minutes
  3. customThe mixture is then partitioned between ether and water
  4. washthe organic layer is washed with water and brine before it
  5. dry with materialis dried (Na2SO4)
  6. filtrationThe mixture is then filtered
  7. customThe title material is then purified by column chromatography

Sources & evidence

ORD record
ord-410f26e01ef342aba88a683bd1dd4816
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

Loading…