Sodium borohydride → HCID 18945165, compound

HRID 399856Notes

Reaction equation

HRID 399856 reaction equation
[C:1](/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])([OH:3])=[O:2].[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]([CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:17]=[CH:18][CH:19]=[CH:20]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18945123HCID 18945123, compound

Product 1

HCID 18945165HCID 18945165, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of methyl 3-((E)-2-carboxyethenyl)-5-(pyrrol-1-yl)benzoate (1.9 g) and nickel(II) chloride in methanol (40 ml) was added portionwise sodium borohydride (1.24 g). After stirring for 7 hours at room temperature, the reaction mixture was filtered and poured into water, followed by acidification of the solution to pH 2. The resulting precipitate was collected by filtration and washed with water to give methyl 3-(2-carboxyethyl)-5-(pyrrol-1-yl)benzoate (1.72 g).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionpoured into water
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-3e6f56b03bc74242b6d80827b8d46661
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…