Tetrahydrofuran → HCID 22988250, compound

HRID 987161Notes

Reaction equation

HRID 987161 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14](=[O:16])[CH3:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2].B.C1COCC1.C1COCC1>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]([OH:16])[CH3:15])[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 22988240HCID 22988240, compound

Product 1

HCID 22988250HCID 22988250, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An oven-dried round bottom flask fitted with a magnetic stirring bar was charged with compound methyl 5-nitro-3-acetylbenzoate (0,5 g), prepared in step 1 of Intermediate 13, BH3THF (1 M solution in THF, 5 mol equiv.), and anhydrous THF. After stirring at room temperature for 24 h, H2O (20 mL) was added and the solution was concentrated in vacuo. The residue was taken in H2O (20 mL) and extracted with CHCl3 (3×100 mL). The combined CH2Cl2 extracts were washed with saturated Na2CO3 solution (20 mL), dried over Na2SO4 and filtered. The solvent was removed in vacuo to afford product. This was used in the next step without further purification.

Workup

  1. customAn oven-dried round bottom flask fitted with a magnetic stirring bar
  2. concentrationthe solution was concentrated in vacuo
  3. extractionextracted with CHCl3 (3×100 mL)
  4. washThe combined CH2Cl2 extracts were washed with saturated Na2CO3 solution (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customto afford product
  9. customThis was used in the next step without further purification

Sources & evidence

ORD record
ord-170f7d8ae1ee481783a47ad7a52eebb9
Source dataset
uspto-grants-2003_10
Patent number
US06630496B1

Reaction notes

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