Diethyl Ether → HCID 19857105, compound

HRID 2073467Notes

Reaction equation

HRID 2073467 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([C:14]([CH2:27][CH3:28])([P:23]([OH:26])([OH:25])=[O:24])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1)[CH3:13].C(OCC)C>ClCCl>[CH2:27]([C:14]([CH2:12][CH3:13])([P:23]([OH:25])([OH:26])=[O:24])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1)[CH3:28]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 56976335HCID 56976335, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19857105HCID 19857105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (110 mmol) in dichloromethane (150 mL) was rapidly stirred while 4-(diethyl phosphonomethyl)benzyl alcohol (73.6 mmol) in dichloromethane (15 mL) was rapidly added. After 1.5 hours, ethyl ether (200 mL) was added to the reaction mixture and the organic solution was decanted from the tarry residue. The residue was washed with 3×50 mL ethyl ether. The combined organic solution was filtered through Florisil chromatographic material and concentrated to a brown oil. The oil was then distilled to give the product as a clear oil (BP 150°-180° C. @0.002-0.005 mm Hq).

Workup

  1. additionwas rapidly added
  2. customthe organic solution was decanted from the tarry residue
  3. washThe residue was washed with 3×50 mL ethyl ether
  4. filtrationThe combined organic solution was filtered through Florisil chromatographic material
  5. concentrationconcentrated to a brown oil
  6. distillationThe oil was then distilled

Sources & evidence

ORD record
ord-74f5e83b506c4a2da4adadf0f9ac868e
Source dataset
uspto-grants-1990_04
Patent number
US04918064

Reaction notes

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