Water → HCID 9819936, compound

HRID 1743029Notes

Reaction equation

HRID 1743029 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[N:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:34][CH2:35][CH3:36])=[C:28]([O:31][CH2:32][CH3:33])[CH:29]=3)[CH:24]=[C:23]([C:37](OC)=[O:38])[C:22]=2[C:41](OC)=[O:42])=[CH:17][CH:16]=1.[OH-].[Na+].O>C1(C)C=CC=CC=1.O1CCCC1.C(Cl)Cl>[N:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:34][CH2:35][CH3:36])=[C:28]([O:31][CH2:32][CH3:33])[CH:29]=3)[CH:24]=[C:23]([CH2:37][OH:38])[C:22]=2[CH2:41][OH:42])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15224775HCID 15224775, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

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 3.4M solution of sodium bis(methoxyethoxy)aluminumhydride 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 time for 15 minutes. The reaction solution is warmed, and stirred under ice-cooling for 1.5 hour, and thereto is added 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-46cdcc670a9c41d28551c01aaddc1b1c
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Reaction notes

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