Sodium borohydride → HCID 54527314, compound

HRID 1579606Notes

Reaction equation

HRID 1579606 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:16][C:15]([C:17]([CH3:19])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]>CO>[CH3:19][CH:17]([OH:18])[C:15]1[O:16][C:12]([C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44054061-[5-(4-Nitro-phenyl)-furan-2-yl]-ethanone

Product 1

HCID 54527314HCID 54527314, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (9.0 g, 0.34 mole) was added in portions to a stirred mixture of 55 g (0.24 mole) of methyl 5-(p-nitrophenyl)-2-furyl ketone in 700 ml of methanol at 20°-25° over 45 minutes. The mixture was stirred at ambient temperature for 4 hours and allowed to stand overnight. Some insoluble material was removed by filtration and discarded. The filtrate was poured into a mixture of ice and water (3 liters) and made acidific with 5% aqueous HCl. The brown oil which was deposited solidified on standing and was collected by filtration to give 56 g (100%) of title compound. Recrystallization from a cyclohexane-benzene mixture gave an analytical sample, m.p. 69.5°-70.5°.

Workup

  1. waitto stand overnight
  2. customSome insoluble material was removed by filtration
  3. additionThe filtrate was poured into a mixture of ice and water (3 liters)
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-9415bec5a3b94d599c3f1d7df2b173f2
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

Loading…