Sodium hydride → HCID 13945820, compound

HRID 1252839Notes

Reaction equation

HRID 1252839 reaction equation
[H-].[Na+].[CH2:3]([O:10][P:11]([O-:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:21]1([CH2:27][CH2:28][CH2:29][CH2:30]Cl)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[C:21]1([CH2:27][CH2:28][CH2:29][CH2:30][P:11](=[O:20])([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78543(4-Chlorobutyl)benzeneHCID 21904359Dibenzylphosphite

Product 1

HCID 13945820HCID 13945820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride 50% oil dispersion (1.01 g., 20.8 mmole) is added to a solution of dibenzylphosphite (5.25 g., 20.0 mmole) in dry dimethylformamide (30 ml.) under argon. The resulting mixture is stirred at room temperature for one hour and at 40° (bath temperature) for 30 minutes. The resulting clear, yellow solution is allowed to cool to room temperature and treated with a solution of 4-phenylbutyl chloride (4.0 g., 23.7 mmole) in dimethylformamide (3 ml.). The resulting mixture is stirred at room temperature for 18 hours and at 40° for 2 hours. The mixture is partitioned between ethyl acetate-1% potassium bisulfate. The organic phase is washed successively with water (twice), saturated sodium bicarbonate (twice), and saturated sodium chloride (twice), dried over sodium sulfate, and evaporated. The residue is purified by flash chromatography (silica gel, 100 g. of LPS-1) eluting with ethyl acetate:hexane (3:7) to give (4-phenylbutyl)phosphonic acid, dibenzyl ester as a colorless, somewhat viscous oil.

Workup

  1. temperatureto cool to room temperature
  2. stirringThe resulting mixture is stirred at room temperature for 18 hours and at 40° for 2 hours
  3. customThe mixture is partitioned between ethyl acetate-1% potassium bisulfate
  4. washThe organic phase is washed successively with water (twice), saturated sodium bicarbonate (twice), and saturated sodium chloride (twice),
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is purified by flash chromatography (silica gel, 100 g. of LPS-1)
  8. washeluting with ethyl acetate:hexane (3:7)

Sources & evidence

ORD record
ord-e109fa1223c24e17931789ff2609e534
Source dataset
uspto-grants-1988_05
Patent number
US04745196

Reaction notes

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