Water → HCID 23118299, compound

HRID 1987780Notes

Reaction equation

HRID 1987780 reaction equation
[N+:1]([C:4]1[C:5]([CH3:20])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18]C)([CH3:16])[CH2:8][CH2:7]2)([O-:3])=[O:2].[B].O>C(Cl)Cl>[N+:1]([C:4]1[C:5]([CH3:20])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][OH:18])([CH3:16])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5462311BoronHCID 23118293HCID 23118293, compound

Product 1

HCID 23118299HCID 23118299, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

9.5 g of 6-nitro-2-methoxymethyl-2,5,7,8-tetramethylchroman was dissolved in 80 ml of methylene chloride and 31.4 ml of a 1M boron tribromidemethylene chloride solution was added under a nitrogen gas flow at 0° C., followed by stirring at 0° C. for 3 hours. After the completion of the reaction, the reaction solution was poured into water and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 4.5 g of the objective product.

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing magnesium sulfate
  6. filtrationby filtration
  7. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-6f47813eb5234343a6406a40cb324bd3
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

Loading…