Tetrahydrofuran → HCID 67509069, compound

HRID 623523Notes

Reaction equation

HRID 623523 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=1/[CH:4]=[N:5]/[S@:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7].[CH3:20][Mg]Br.C1COCC1>ClCCl>[F:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][C:3]=1[CH:4]([NH:5][S@:6]([C:8]([CH3:11])([CH3:9])[CH3:10])=[O:7])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 87426708HCID 87426708, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67509069HCID 67509069, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S,E)-N-(2-fluoro-5-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide (single enantiomer) (150 mg, 0.51 mmol, Step-1) in dichloromethane (5 mL) is added dropwise a solution of methylmagnesium bromide in THF (0.99 M, 2.57 mL, 2.54 mmol) at −78° C. The resulting mixture is stirred at −78° C. for 2 hours and at room temperature for 1 hour. The reaction is quenched by saturated aqueous ammonium chloride solution (50 mL), and the aqueous phase is extracted with EtOAc (50 mL×2). The combined organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (3:1-1:1) to give 63 mg (40% yield) of the title compound as a white solid.

Workup

  1. customThe reaction is quenched by saturated aqueous ammonium chloride solution (50 mL)
  2. extractionthe aqueous phase is extracted with EtOAc (50 mL×2)
  3. dry with materialThe combined organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (3:1-1:1)

Sources & evidence

ORD record
ord-73c02f3cfe334c0eac78b3eb6ef1cab4
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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