Sodium borohydride → HCID 570416, compound

HRID 1840312Notes

Reaction equation

HRID 1840312 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16]C=2)O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO>[OH:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C:12]1[CH:14]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23447931HCID 23447931, compound

Product 1

HCID 570416HCID 570416, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-nitrobenzoin (4.55 g, 20.1 mmol) was dissolved in 70 ml of anhydrous methanol cooled down to 0° C. in an ice bath, NaBH4 (0.915 g, 24.2 mmol) was then added under N2, the mixture was stirred at r.t., for overnight, quenched with NH4Cl sat'd aqueous solution, MeOH was evaporated and EtOAc was added, the mixture was washed with water, the organic layer was dried over MgSO4 and concentrated to give a solid as the desired product(˜4.58 g, ˜100% yield).

Workup

  1. customquenched with NH4Cl
  2. customwas evaporated
  3. additionEtOAc was added
  4. washthe mixture was washed with water
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b454e10d5104ff0a224868b0b51ad94
Source dataset
uspto-grants-2004_01
Patent number
US06680321B1

Reaction notes

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