Ammonium Chloride → HCID 90417249, compound

HRID 633577Notes

Reaction equation

HRID 633577 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH:13]1[CH2:15][CH2:14]1.[CH:16]([Mg]Br)=[CH2:17].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[C:3]([O:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[CH:4][CH:5]=[C:6]2[C:7]=1[NH:8][CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 90416340HCID 90416340, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 90417249HCID 90417249, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

A 250 mL roundbottom flask with stirbar was charged with a solution of Example 98A (6.18 g, 22.7 mmol) in tetrahydrofuran (80 mL) and cooled to −45° C. under nitrogen. A solution of 0.7 M vinylmagnesium bromide in tetrahydrofuran (100 mL, 70.0 mmol) was added over 20 minutes and the mixture stirred at −45° C. for 30 minutes. The mixture was then poured into aqueous ammonium chloride and extracted with 3×150 mL of ether. The combined organics were dried over anhydrous magnesium sulfate. After filtration and solvent removal the residues were adsorbed on silica gel and chromatographed on a 150 g silica cartridge eluting with 0-10-100% ethyl acetate/heptane to provide 3.087 g, (51%) of the title compound.

Workup

  1. extractionextracted with 3×150 mL of ether
  2. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration and solvent removal the residues
  4. customchromatographed on a 150 g silica cartridge
  5. washeluting with 0-10-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-47dc17ca3f9547268b03e072d2cef48b
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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