Ammonium Chloride → HCID 21998738, compound

HRID 1976788Notes

Reaction equation

HRID 1976788 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=1)(=[O:5])=[O:4].[CH2:19]([Mg]Br)[CH:20]=C.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]([F:18])([F:17])[S:3]([O:6][C:7]1[CH:12]=[C:11]2[C:10](=[C:9]([CH3:16])[CH:8]=1)[NH:13][CH:20]=[CH:19]2)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12134725HCID 12134725, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 21998738HCID 21998738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-methyl-4-nitrophenyl trifluoromethanesulfonate (8.96 g, 31.4 mmol) in THF (200 mL) at 0° C. was treated dropwise with 1M allylmagnesium bromide in THF (110 mL 110 mmol), stirred for 2 hours, transferred into saturated NH4Cl (200 mL), and extracted with ethyl acetate (200 mL). The extract was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography with 9:1 hexanes/ethyl acetate to provide 3.19 g of the desired product.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. dry with materialThe extract was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography with 9:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-1b37775ff04748529871e26b7b553d2b
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

Loading…