Tetrahydrofuran → HCID 45137726, compound

HRID 221380Notes

Reaction equation

HRID 221380 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22](OC)=[O:23])(=[O:17])=[O:16])=[CH:11][CH:10]=1.C[Mg]I.[CH2:32]1COC[CH2:33]1>O.C(OCC)(=O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:28]=[CH:27][CH:26]=[C:21]([C:22]3([OH:23])[CH2:33][CH2:32]3)[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 67329527HCID 67329527, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 45137726HCID 45137726, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)benzoate (500 mg, 1.03 mmol) and titanium isopropoxide (61 μL, 0.206 mmol) in anhydrous THF (10 mL) was cooled under nitrogen to −10° C. A solution of 3 Methylmagnesium iodide in THF (2.4 mL, 7.2 mmol) was added by syringe and the solution was stirred at 0° C. for 1 hour, then at room temperature overnight. The mixture was diluted with water (5 mL) and ethyl acetate (20 mL) and filtered through Celite. The layers were separated. The organic phase was washed with water (10 mL) and brine (10 mL) and dried over MgSO4. Evaporation of the solvents gave an orange gum which was purified by column chromatography on silica, eluting with acetone/hexane (1:4) and the title compound obtained as a light yellow foam (100 mg). 1H NMR (300 MHz, CDCl3): δ 0.95-1.05 (2H, m), 1.20-1.24 (2H, m), 6.90-7.10 (3H, m), 7.20-7.46 (3H, m), 7.47-7.48 (3H, m) and 7.83 (2H, d). MS, m/z: Calcd, 433.031. Found, 433.22 (M).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationfiltered through Celite
  4. customThe layers were separated
  5. washThe organic phase was washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvents
  8. customgave an orange gum which
  9. customwas purified by column chromatography on silica
  10. washeluting with acetone/hexane (1:4)

Sources & evidence

ORD record
ord-5ef378e22b3940df8259ecbba9ca4b22
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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