Water → HCID 59134415, compound

HRID 1993485Notes

Reaction equation

HRID 1993485 reaction equation
Br[C@H:2]1[C@H:7]([OH:8])[C:6]2[CH:9]=[C:10]([N+:17]([O-:19])=[O:18])[C:11]([O:13][CH2:14][O:15][CH3:16])=[CH:12][C:5]=2[O:4][C:3]1([CH3:21])[CH3:20].[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 86617190HCID 86617190, compound

Product 1

HCID 59134415HCID 59134415, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (±)-trans-3-bromo-7-methoxymethoxy-2,2-dimethyl-6-nitro-3,4-dihydro-2H-1-benzopyran-4-ol (550 mg, 1.52 mmol) in dioxane (5.5 mL), 1 mol/L aqueous sodium hydroxide 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 aqueous sodium thiosulfate 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 aqueous sodium thiosulfate 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-51be984ac6d347018dd0a7c0bd534a64
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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