Water → HCID 17906295, compound

HRID 852087Notes

Reaction equation

HRID 852087 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[CH2:19]1[O:21][C@H:20]1[CH2:22]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.O>CN(C)C=O>[S:3]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:22][CH:20]3[CH2:19][O:21]3)=[CH:12][CH:13]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 232269524-Benzo[b]thien-3-ylphenol

Product 1

HCID 17906295HCID 17906295, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Cool a mixture of sodium hydride (585 mg, 60% dispersion in mineral oil, 14.6 mmol) in dimethylformamide (20 mL, anhydrous), with an ice bath, under a nitrogen atmosphere. Add a solution of 4-benzo[b]thiophen-3-yl-phenol (3.0 g, 13.3 mmol) in dimethylformamide (20 mL) over a period of 5 minutes. Reaction mixture has noticeable gas evolution and is a yellow mixture. Stir at room temperature for 0.5 hours and cool via an ice bath to give a yellow solution. Rapidly, add a solution of (2R)-(−)-glycidyl 3-nitrobenzenesulfonate (3.78 g, 14.6 mmol) in dimethylformamide (20 mL) and stir at 0° C. for 35 minutes. The reaction mixture is a red-orange color. Stir reaction mixture at room temperature overnight. Pour the reaction mixture into cold (0° C.) water (300 mL) and extract with ethyl acetate (3×100 mL). Combine the organic layers, wash with water (100 mL), saturated sodium chloride (100 mL), dry (MgSO4) and concentrate (in vacuo) to give a brown oil. The brown oil is purified by column chromatography (dichloromethane) to give a light green/clear, viscous oil. The oil is dried (0.5 mm Hg) at room temperature for 3 hours to give the title compound as a solid (3.19 g, 85% Yield).

Workup

  1. temperatureCool
  2. customReaction mixture
  3. temperaturecool via an ice bath
  4. customto give a yellow solution
  5. stirringstir at 0° C. for 35 minutes
  6. stirringStir
  7. customreaction mixture at room temperature overnight
  8. extractionextract with ethyl acetate (3×100 mL)
  9. washCombine the organic layers, wash with water (100 mL), saturated sodium chloride (100 mL)
  10. dry with materialdry (MgSO4)
  11. concentrationconcentrate (in vacuo)
  12. customto give a brown oil
  13. customThe brown oil is purified by column chromatography (dichloromethane)
  14. customto give a light green/clear, viscous oil
  15. customThe oil is dried (0.5 mm Hg) at room temperature for 3 hours

Sources & evidence

ORD record
ord-248ff0b7a0f24412bd3fef97a29cd3be
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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