Acetone → 1,10-Phenanthroline-2,9-diyldimethanol

HRID 1904194Notes

Reaction equation

HRID 1904194 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[N:7]N(C=O)[CH2:9][CH:10]=3)[C:5]=2C=1)=[O:2].[CH2:19]([OH:21])[CH3:20].[BH4-].[Na+].CC(C)=O.C[N:29](C=O)C>>[OH:21][CH2:19][C:20]1[CH:9]=[CH:10][C:11]2[C:6](=[C:5]3[C:14](=[CH:13][CH:12]=2)[CH:15]=[CH:16][C:3]([CH2:1][OH:2])=[N:29]3)[N:7]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 702EthanolHCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 86743106HCID 86743106, compound

Product 1

HCID 3369121,10-Phenanthroline-2,9-diyldimethanol

Conditions

Temperature
30 °C

Procedure

To a mixture of 2.0 g of dialdehyde 26 in 40 mL of DMF and 5 Ml of ethanol was added 800 mg of NaBH4. The solution was stirred 6 hours at 30° C. then 5 mL of acetone was added. The solvent was removed under vacuum and the residue recrystallized from 50 mL of H2O to yield 1.7 g of diol (27). 1H NMR (DMSO-d6) 4.7 (s, 4H); 5.45 (broad s, 2H); 7.6 (ABq, 2H); 7.7 (s, 2H); 8.25 (ABq, 2H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue recrystallized from 50 mL of H2O

Sources & evidence

ORD record
ord-e21131ebd43c4ddc8271534efefc3171
Source dataset
uspto-grants-1989_06
Patent number
US04837169

Reaction notes

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