Water → HCID 15097265, compound

HRID 329527Notes

Reaction equation

HRID 329527 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[CH2:9][OH:10].[H-].[Na+].[OH2:26]>CN(C)C=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[CH2:9][O:10][CH2:9][C:8]1[O:26][CH2:14][CH2:13][CH2:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 15097263HCID 15097263, compound

Product 1

HCID 15097265HCID 15097265, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 1.049 g of 2,8-bis(tetrahydropyran-2-yloxy)-1-octanol (prepared as described in Preparation 72) in 10 ml of dimethylformamide was added, whilst ice-cooling, to a mixture of 0.152 g of sodium hydride (as a 55% dispersion in mineral oil) and 10 ml of dimethylformamide. The mixture was then stirred at room temperature for 1 hour. At the end of this time, a solution of the residue prepared as described in step (a) above dissolved in 15 ml of dimethylformamide was added to the mixture, which was then stirred at room temperature for 19 hours. It was then poured into 350 ml of water and extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 60 g of silica gel. 0.934 g of the title compound was obtained, as a colorless oil, from the fractions eluted with a 9:1 by volume mixture of hexane and ethyl acetate.

Workup

  1. customAt the end of this time, a solution of the residue prepared
  2. additionwas added to the mixture, which
  3. stirringwas then stirred at room temperature for 19 hours
  4. extractionextracted twice with ethyl acetate
  5. washThe combined extracts were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-37e6df0ac5eb473f9b56845dad2fad03
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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