Sodium hydride → HCID 54537869, compound

HRID 1086381Notes

Reaction equation

HRID 1086381 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)(=[O:5])[CH3:4].[CH3:18][S:19]([C:22]1[CH:34]=[CH:33][C:25]([CH2:26]P(=O)(OC)OC)=[CH:24][CH:23]=1)(=[O:21])=[O:20]>COCCOC>[C:3]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH:26][C:25]2[CH:24]=[CH:23][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:34][CH:33]=2)=[CH:12][CH:11]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18939124HCID 18939124, compoundHCID 19818839Dimethyl {[4-(methanesulfonyl)phenyl]methyl}phosphonate

Product 1

HCID 54537869HCID 54537869, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 3.0 g (0.075 mol) of 60% sodium hydride dispersion, 11.0 g (0.05 mol) of 4-(2-acetoxyethoxy)benzaldehyde (Example 1) and 125 mL of dry 1,2-dimethoxyethane were added, under nitrogen, 13.9 g (0.05 mol) of dimethyl 4-methylsulfonylbenzylphosphonate. The mixture was heated at reflux for 2 hr, after which time it was cooled and poured over ca. 200 g of crushed ice under nitrogen. The crude product was filtered, washed with water and air-dried to give 17.7 g (98%) of the white solid, which was used without further purification. m.p.=175°-177° C.

Workup

  1. additionwere added, under nitrogen
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hr
  4. temperatureafter which time it was cooled
  5. filtrationThe crude product was filtered
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-af3de8f832e34080a2feac39eb1800d7
Source dataset
uspto-grants-1991_07
Patent number
US05029979

Reaction notes

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