Hydrochloric Acid → HCID 20479545, compound

HRID 1649348Notes

Reaction equation

HRID 1649348 reaction equation
[CH2:1]([O:3][P:4]([CH2:22][C:23]([O:25]C)=[O:24])([CH:6]([CH2:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])[CH3:2].Cl>C(O)(=O)C>[CH2:1]([O:3][P:4]([CH2:22][C:23]([OH:25])=[O:24])([CH:6]([CH2:13][C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86738848HCID 86738848, compound

Product 1

HCID 20479545HCID 20479545, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product from part (b) (3.10 g., 8.115 mmole) in glacial acetic acid (10 ml.) is treated with concentrated hydrochloric acid (5 ml.) and stirred at room temperature for 46 hours. The mixture is poured onto an ice-water mixture and extracted with ethyl acetate. The ethyl acetate extract is washed with water, saturated sodium chloride solution, dried over Na2SO4 and evaporated. The residue is purified by flash chromatography on silica gel (85 g.) eluting with acetic acid/methanol/dichloromethane (0.5:3.0:100) to give 470 mg. of recovered starting material and 2.0 g. of [ethoxy[1-(2-oxo-2-phenylethyl)heptyl]phosphinyl]acetic acid as a colorless glass, Rf (acetic acid/methanol/dichloromethane 0.5:5:100) 0.32.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed with water, saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue is purified by flash chromatography on silica gel (85 g.)
  7. washeluting with acetic acid/methanol/dichloromethane (0.5:3.0:100)
  8. customto give 470 mg
  9. customof recovered

Sources & evidence

ORD record
ord-dfd1e138af6649f59caa4adc4f72609f
Source dataset
uspto-grants-1983_11
Patent number
US04416833

Reaction notes

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