Water → HCID 59134415, compound

HRID 2425361Notes

Reaction equation

HRID 2425361 reaction equation
Br[C:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]2[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:6]=2[C:7]=1[OH:8].[OH-].[Na+].O>O1CCOCC1>[O:8]1[CH:7]2[CH:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:6]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67246089HCID 67246089, compound

Product 1

HCID 59134415HCID 59134415, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-7-methoxymethoxy-2,2-dimethyl-6-nitro-1-benzopyran-4-ol (550 mg, 1.52 mmol) in dioxane (5.5 mL), 1 mol/L sodium hydroxide aqueous solution (1.82 mL, 1.82 mmol) was added at room temperature, and the resulting mixture was stirred for 2 hours. Upon the completion of the reaction, water was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium thiosulfate aqueous solution and then with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=4/1) and the aimed product was obtained (yield: 78%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium thiosulfate aqueous solution
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-6c476bd3a5584d9ba3e36e807b3d45ff
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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