Sodium hydride → HCID 58929474, compound

HRID 852870Notes

Reaction equation

HRID 852870 reaction equation
[CH3:1][O:2][P:3]([O-:6])[O:4][CH3:5].[H-].[Na+].[O:9]([CH2:16][CH2:17][CH2:18]Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH3:1][O:2][P:3]([CH2:18][CH2:17][CH2:16][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68522Benzene, (3-bromopropoxy)-HCID 21884954Dimethylphosphite

Product 1

HCID 58929474HCID 58929474, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylphosphite (5.0 g, 45 mmol) was cautiously added to a suspension of NaH (60% dispersion, 2.0 g, 50 mmol) in DMF (45 mL) at 0°. After 2 h, 3-phenoxy propylbromide (10.75 g, 50 mmol) was added, and the mixture stirred at rt for 48 h. The solvent was removed under reduced pressure, the residue dissolved in water (100 mL), extracted with Et2O, and the combined extracts washed with water, brine and dried (MgSO4). The solution was concentrated at reduced pressure to give 10.28 g of crude product. A portion of the crude material (5 g) was distilled to afford 52 (3.4 g, 63%) as a colourless oil. 13C NMR (CDCl3) δ 21.4 (d, J=141.8 Hz), 22.7 (d, J=4.5 Hz), 52.5 (d, J=6.8 Hz), 67.2 (d, J=15 Hz), 114.6, 121.0, 129.6, 158.8. ESMS 245 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water (100 mL)
  3. extractionextracted with Et2O
  4. washthe combined extracts washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationThe solution was concentrated at reduced pressure
  7. customto give 10.28 g of crude product
  8. distillationA portion of the crude material (5 g) was distilled

Sources & evidence

ORD record
ord-4ce6aa31622f480d8686e508e4bcfb60
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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