Sodium hydride → HCID 54525740, compound

HRID 1086384Notes

Reaction equation

HRID 1086384 reaction equation
[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9]P(=O)(OC)OC)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].C([O:23][CH2:24][CH2:25][N:26]([CH3:35])[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)(=O)C>COCCOC>[OH:23][CH2:24][CH2:25][N:26]([CH3:35])[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:17][CH:16]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19818839Dimethyl {[4-(methanesulfonyl)phenyl]methyl}phosphonateHCID 53889066HCID 53889066, compound

Product 1

HCID 54525740HCID 54525740, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of dimethyl 4-methylsulfonylbenzylphosphonate prepared as described in Ulman et al U.S. Pat. No. 4,792,208 (6.29 g, 22.6 mmol), 60% sodium hydride dispersion (1.35 g, 33.9 mmol) and 50 mL of dry 1,2-dimethoxyethane (DME) under nitrogen was treated with a solution of 4-[(2-acetoxyethyl)methylamino]benzaldehyde (5.00 g, 22.6 mmol, Example 5) in 50 mL of DME. The resulting mixture was heated at reflux for 16 hr, then cooled and poured onto 300 g of ice. The resulting yellow solid was filtered, washed with water and air-dried. The solid was heated at reflux in a mixture of 10 g of NaOH, 90 mL of ethanol and 90 mL of water for 24 hr, then cooled and poured onto 200 mL of water. The resulting brown solid was filtered and air-dried. The product was recrystallized twice from a mixture of ethanol and pyridine to produce 4.46 g (60%) of yellow plates, m.p. 201°-204° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 16 hr
  3. temperaturecooled
  4. filtrationThe resulting yellow solid was filtered
  5. washwashed with water
  6. customair-dried
  7. temperatureThe solid was heated
  8. temperatureat reflux in a mixture of 10 g of NaOH, 90 mL of ethanol and 90 mL of water for 24 hr
  9. temperaturecooled
  10. additionpoured onto 200 mL of water
  11. filtrationThe resulting brown solid was filtered
  12. customair-dried
  13. customThe product was recrystallized twice from a mixture of ethanol and pyridine
  14. customto produce 4.46 g (60%) of yellow plates, m.p. 201°-204° C.

Sources & evidence

ORD record
ord-f41c236a6ba54965a7c582edf2856e56
Source dataset
uspto-grants-1991_07
Patent number
US05029979

Reaction notes

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