Water → HCID 15097268, compound

HRID 329531Notes

Reaction equation

HRID 329531 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:4][OH:5].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:20]([O:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:2][OH:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15097267HCID 15097267, compound

Product 1

HCID 15097268HCID 15097268, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.06 g of 2-hydroxymethyl-7-(2-methoxyethoxy)methoxy-1-heptanol (prepared as described in Preparation 80) dissolved in 20 ml of dimethylformamide was added dropwise to 587 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) dispersed in 40 ml of dimethylformamide, whilst ice-cooling (at 5° to 7° C.). The mixture was then stirred at room temperature for 1 hour, after which 1.60 ml of benzyl bromide were added dropwise, whilst ice-cooling (at 5° to 7° C.) The reaction mixture was stirred at room temperature for 2 hours, after which it was poured into 300 ml of water and then extracted five times with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting oily residue was subjected to column chromatography through 60 g of silica gel, and 2.37 g of the title compound were obtained, as a colorless oil, from the fractions eluted with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:1 by volume.

Workup

  1. temperaturecooling (at 5° to 7° C.)
  2. temperaturecooling (at 5° to 7° C.) The reaction mixture
  3. stirringwas stirred at room temperature for 2 hours
  4. extractionextracted five times 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-1653252c2c8b45b8b28afd8dc437461f
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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