Ammonium Chloride → HCID 59543159, compound

HRID 1970970Notes

Reaction equation

HRID 1970970 reaction equation
[OH:1][C:2]([CH3:13])([CH3:12])[CH2:3]/[CH:4]=[N:5]/[S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1.[NH4+].[Cl-]>C(Cl)Cl>[CH:14]1([CH:4]([NH:5][S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[CH2:3][C:2]([OH:1])([CH3:13])[CH3:12])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59543125HCID 59543125, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 59543159HCID 59543159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[(1E)-3-hydroxy-3-methylbutylidene]-2-methylpropane-2-sulfinamide (0.6 g, 2.9 mmol) in DCM (18 mL) was added cyclopropylmagnesium bromide (0.5 M in THF, 17.5 mL, 8.8 mmol) at −78° C. The reaction mixture was allowed to warm to room temperature as the bath did (2 h). The mixture was treated with sat'd NH4Cl solution, and extracted with EtOAc. The organic layer was washed with brine, dried (sodium sulfate), concentrated, and purified by flash chromatography to give the title compound.

Workup

  1. custom(2 h)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fe1481c8b36147248a081a89bef61895
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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