HCID 2806137, compound → HCID 53907224, compound

HRID 1579608Notes

Reaction equation

HRID 1579608 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[CH:9][CH:10]=1)=[O:5]>CO>[Cl:18][C:13]1[CH:12]=[C:11]([C:8]2[O:7][C:6]([CH:4]([OH:5])[CH3:3])=[CH:10][CH:9]=2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

4

Reactant 2

HCID 2806137HCID 2806137, compoundHCID 4311764Sodium borohydride

Product 1

HCID 53907224HCID 53907224, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium Borohydride (1.5 g, 0.04 mole) was added in portions to a stirred mixture of 15 g (0.059 mole) of 5-(3,4-dichlorophenyl)-2-furyl methyl ketone and 125 ml of MeOH at 15°-20° over 30 minutes. The mixture was stirred at ambient temperature for 3 hours. Some insoluble material was removed by filtration and set aside. The filtrate was poured into 300 ml of ice-H2O mixture and made acidic with dilute HCl. The oil which was deposited solidified and was collected by filtration. Recrystallization from n-hexane gave 11 g (73%) of title compound, m.p. 82.5°-83.5°.

Workup

  1. customSome insoluble material was removed by filtration
  2. additionThe filtrate was poured into 300 ml of ice-H2O mixture
  3. filtrationwas collected by filtration
  4. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-0b36095fb92d492a96ff7e2987b657ba
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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