Water → HCID 9819936, compound

HRID 1740653Notes

Reaction equation

HRID 1740653 reaction equation
[Al].[Na].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH2:23][CH3:24])=[C:16]([O:19][CH2:20][CH3:21])[CH:17]=3)[CH:12]=[C:11]([C:25](OC)=[O:26])[C:10]=2[C:29](OC)=[O:30])=[CH:5][CH:4]=1.[OH-].[Na+].O>C1(C)C=CC=CC=1.O1CCCC1.C(Cl)Cl>[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:22][CH2:23][CH3:24])=[C:16]([O:19][CH2:20][CH3:21])[CH:17]=3)[CH:12]=[C:11]([CH2:25][OH:26])[C:10]=2[CH2:29][OH:30])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15224775HCID 15224775, compoundHCID 45051913HCID 45051913, compound

Product 1

HCID 9819936HCID 9819936, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To tetrahydrofuran (25 ml) is added a 3.4 M solution of sodium aluminum bis(methoxyethxoy) hydride in toluene (18.0 ml), and the mixture is cooled to -10° C. To the mixture is added dropwise a suspension of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-diethoxynaphthalene (10.0 g) in tetrahydrofuran (25 ml) over a period of 15 minutes. The reaction solution is warmed, and stirred under ice-cooling for 1.5 hour, and thereto is added a 15% aqueous sodium hydroxide solution (3.7 ml). To the reaction mixture are added water and methylene chloride, and the insoluble materials are removed by filtration. The filtrate is extracted with methylene chloride, and the extract is washed, dried, and concentrated to give 1-(4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-diethoxynaphthalene (7.89 g).

Workup

  1. additionTo the mixture is added dropwise
  2. temperatureThe reaction solution is warmed
  3. temperaturecooling for 1.5 hour
  4. customthe insoluble materials are removed by filtration
  5. extractionThe filtrate is extracted with methylene chloride
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-63763f018d3c4e60b8c45ffa6ce6b6b7
Source dataset
uspto-grants-1999_10
Patent number
US05969140

Reaction notes

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