Water → HCID 19009246, compound

HRID 1742496Notes

Reaction equation

HRID 1742496 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1[CH:17]=[CH2:18].[OH2:19]>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1[CH2:17][CH2:18][OH:19]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10727374HCID 10727374, compound

Product 1

HCID 19009246HCID 19009246, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

1.61 g of titanium tetrachloride were added to a mixture of 0.65 g of sodium borohydride and 20 ml of dry ethylene glycol dimethyl ether, and the resulting mixture was stirred at room temperature for 1 hour. A solution of 1.83 g of 1,4-dimethoxy-2-vinylnaphthalene [prepared as described in step (b) above] in 40 ml of dry ethylene glycol dimethyl ether was then added dropwise to the resulting mixture, and the mixture was stirred for 21 hours. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.40 g of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 21 hours
  2. extractionafter which it was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-b586f95c9a83473d922713611e1fb4e1
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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