Tetrahydrofuran → 1346819-23-5

HRID 1406296Notes

Reaction equation

HRID 1406296 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=[O:8])=[N:4][CH:3]=1.[CH2:9]1COCC1.C[Mg+].[Br-]>C(OCC)C>[Br:1][C:2]1[S:6][C:5]([CH:7]([OH:8])[CH3:9])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 263704275-Bromo-1,3-thiazole-2-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 662228301346819-23-5

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice cold solution of 5-bromothiazole-2-carbaldehyde (3 g, 15.6 mmol) in diethyl ether (20 mL) was added a THF solution of MeMgBr (3M, 50 ml, 150 mmol). Solid was produced rapidly. LCMS showed a new product with desired mass. The reaction was quenched with saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by ISCO CombiFlash® chromatography eluting 10-40% ethyl acetate in heptanes. The title compound was obtained as a viscous yellow oil (3.25 g, 62% yield).

Workup

  1. customSolid was produced rapidly
  2. customThe reaction was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by ISCO CombiFlash® chromatography
  8. washeluting 10-40% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-c85fe61427a74e27b5dd459493e693a5
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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