Water → HCID 68783646, compound

HRID 2364772Notes

Reaction equation

HRID 2364772 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[CH2:11][CH2:12][C:13](C2C=CC([N+]([O-])=O)=CC=2)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:24])[CH2:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 137628911,4-Bis(4-nitrophenyl)butane-1,4-dione

Product 1

HCID 68783646HCID 68783646, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Example 1A (1.0 g, 3.05 mmol) in anhydrous THF (30 ml) at 0° C. was added sodium borohydride (0.357 g, 9.44 mmol). The resulting mixture was stirred at 50° C. overnight. The cooled mixture was poured into water, extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to give a tan solid that was collected by filtration and dried to give the title compound (0.82 gm, 81% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid was triturated with dichloromethane
  6. customto give a tan solid
  7. filtrationthat was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-7c8847534f2742e6ad8adca716763469
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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