Water → HCID 19006234, compound

HRID 1743032Notes

Reaction equation

HRID 1743032 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][OH:24])[C:10]=2[CH2:25][OH:26])[CH:4]=1.S(C1C=CC(C)=CC=1)(O[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=O)=O.O>CN(C)P(=O)(N(C)C)N(C)C>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH:12]=[C:11]([CH2:23][O:24][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:10]=2[CH2:25][OH:26])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 283345Neopentyl tosylateHCID 15224777HCID 15224777, compound

Product 1

HCID 19006234HCID 19006234, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

To a suspension of sodium hydride in hexamethylphosphoric triamide (40 ml) is added a solution of 1-(3-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene in hexamethylphosphoramide (10 ml) under ice-cooling. The mixture is warmed to room temperature, and then stirred for 30 minutes. To the reaction solution is added neo-pentyl tosylate (3.67 g), and the mixture is reacted at 100° C. for 30 minutes. The mixture is allowed to cool, and thereto is added water, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated. The resulting residue is subjected to silica gel column chromatography (eluent; chloroform:acetone=5:1), and the desired fractions are concentrated to give 1-(3-pyridyl)-2-hydroxymethyl-3-neo-pentyloxymethyl-6,7-dimethoxynaphthalene (1.5 g) as an oily product.

Workup

  1. temperaturecooling
  2. customthe mixture is reacted at 100° C. for 30 minutes
  3. temperatureto cool
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. concentrationconcentrated
  8. concentrationthe desired fractions are concentrated

Sources & evidence

ORD record
ord-4acd29f9f95a4b0b90e121a352cda0ce
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Reaction notes

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