Ammonium Chloride → HCID 57420144, compound

HRID 1172834Notes

Reaction equation

HRID 1172834 reaction equation
Cl[C:2]1[N:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:20]([Mg]Cl)[CH2:21][CH3:22].[NH4+].[Cl-]>C1COCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]2[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH2:20][CH2:21][CH3:22])[N:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11522235HCID 11522235, compoundHCID 178455855HCID 178455855, compound

Product 1

HCID 57420144HCID 57420144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of product from Step 2 (73.0 g, 0.245 mol) and Fe(acac)3 (4.3 g, 12.2 mmol) in THF (1.2 L) cooled at −30° C. was added a solution of n-propylmagnesium chloride (2 M in Et2O, 245 mL, 0.49 mol) over 45 min, while maintaining the reaction temperature below −30° C. The dark-colored reaction mixture was stirred for an additional 15 min and poured into a saturated aqueous solution of NH4Cl (1.5 L). The organic layer was separated and washed with brine (1×250 mL). After removal of the solvent, the crude product was purified by chromatography on silica gel eluting with 100% hexane and then with 15:1 hexane:ethyl acetate to furnish the title product as an oil.

Workup

  1. temperaturewhile maintaining the reaction temperature below −30° C
  2. customThe organic layer was separated
  3. washwashed with brine (1×250 mL)
  4. customAfter removal of the solvent
  5. customthe crude product was purified by chromatography on silica gel eluting with 100% hexane

Sources & evidence

ORD record
ord-6b731fb0adb04905a882e1f7bddb8bb2
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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