Water → HCID 9819936, compound

HRID 613033Notes

Reaction equation

HRID 613033 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-0fb1f842aa0e48a4b6d2d8c981369d12
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

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