Sodium hydride → HCID 86735058, compound

HRID 2071661Notes

Reaction equation

HRID 2071661 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH:15]([CH:18]=O)[O:14]1>COCCOC>[CH3:3][O:4][C:5](=[O:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:17][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])[O:14]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 54550798HCID 54550798, compound

Product 1

HCID 86735058HCID 86735058, compoundYield 144.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

50% sodium hydride in mineral oil (1.11 g, 0.0230 mole) was suspended in 1,2-dimethoxyethane (115 ml). At 15° C and under vigorous stirring (2-oxoheptyl)-phosphoric acid dimethyl ester (5.11 g, 0.0230 mole) in dimethoxyethane (23 ml) was added dropwise over a period of 15 minutes. The reaction mixture containing a white voluminous precipitate was stirred for 1 hour at room temperature. A solution of crude II (7.20 g), prepared from I (7.55 g, 0.0250 mole), in 1,2-dimethoxyethane (46 ml) was added dropwise over a period of 15 minutes to the stirred reaction mixture, maintained below 25° C. The resulting turbid, yellow solution was stirred at room temperature for 2 hours. The solvent was distilled off from a water bath (40° C, 10 mm Hg). The oily residue was dissolved in ether (230 ml), washed with cold 10% aqueous sodium chloride (60 + 60 + 60 ml) and cold water (60 + 60 ml), and dried over sodium sulfate. After filtration, the solvent was removed from a water bath (60° C, 10 mm Hg). The residual light tea-coloured oil (9.60 g) was distilled under nitrogen to give 7.15 g (81%) of III as a light yellowish oil, b0.05 160°-190° C, nD25 1.4712.

Workup

  1. additionwas added dropwise over a period of 15 minutes
  2. additionThe reaction mixture containing a white voluminous precipitate
  3. additionwas added dropwise over a period of 15 minutes to the stirred reaction mixture
  4. temperaturemaintained below 25° C
  5. stirringThe resulting turbid, yellow solution was stirred at room temperature for 2 hours
  6. distillationThe solvent was distilled off from a water bath (40° C, 10 mm Hg)
  7. dissolutionThe oily residue was dissolved in ether (230 ml)
  8. washwashed with cold 10% aqueous sodium chloride (60 + 60 + 60 ml) and cold water (60 + 60 ml)
  9. dry with materialdried over sodium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was removed from a water bath (60° C, 10 mm Hg)
  12. distillationThe residual light tea-coloured oil (9.60 g) was distilled under nitrogen

Sources & evidence

ORD record
ord-4316f512e1b14277951b8ae6cdb91b75
Source dataset
uspto-grants-1977_09
Patent number
US04048198

Reaction notes

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