Diethyl benzylphosphonate → HCID 69662858, compound

HRID 2212100Notes

Reaction equation

HRID 2212100 reaction equation
[CH2:1](P(=O)(OCC)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([S:22]([C:25]([CH3:37])([CH3:36])[CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][C:31](=O)[CH2:30]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+]>CN1CCN(C)C1=O>[C:16]1([S:22]([C:25]([CH3:37])([CH3:36])[CH2:26][CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][CH2:32]/[C:33](=[CH:1]/[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)/[CH2:34]2)(=[O:24])=[O:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 69663068HCID 69663068, compound

Product 1

HCID 69662858HCID 69662858, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent2×

Procedure

A solution of diethyl benzylphosphonate (0.53 ml, 2.54 mmol) and 1-(4-benzenesulfonyl-4-methylpentyl)-3-piperidinone (0.7 g, 2.17 mmol) in 1,3-dimethylimidazolidin-2-one (5 ml) was added dropwise to a stirred slurry of sodium hydride (60% dispersion in mineral oil, 117 mg, 2.93 mmol) in 1,3-dimethylimidazolidin-2-one (3 ml). The reaction was stirred for 30 minutes then quenched by the addition of water. The mixture was extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 20–75% ethyl acetate/chloroform, followed by preparative HPLC.

Workup

  1. customthen quenched by the addition of water
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with 20–75% ethyl acetate/chloroform

Sources & evidence

ORD record
ord-10635966876b4f6fa37619521028f383
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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