Hydrochloric Acid → HCID 72732177, compound

HRID 2248009Notes

Reaction equation

HRID 2248009 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH2:8]P(=O)(OCC)OCC)=[O:7])[CH3:4].C[CH2:18][CH2:19][CH:20]([CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O)C.Cl.O1CC[CH2:34][CH2:33]1>>[CH2:3]([O:5][C:6](=[O:7])[CH:8]=[C:33]([C:28]1[CH:27]=[CH:26][C:25]([CH2:23][CH2:22][CH2:20][CH2:19][CH3:18])=[CH:30][CH:29]=1)[CH3:34])[CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran4×HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 53817625HCID 53817625, compound

Product 1

HCID 72732177HCID 72732177, compound

Procedure

Sodium hydride (28.69, content: 63%) was suspended in tetrahydrofuran (1000 ml). Diethyl ethoxycarbonylmethylphosphonate (168 g) dissolved in tetrahydrofuran (500 ml) was added dropwise into the mixture with cooling in an ice-bath over 30 mins. 4-Pentylacetophenone (95 g) in tetrahydrofuran (500 ml) was added to the solution. The solution was stirred overnight at a room temperature and then refluxed at 8 hrs. Tetrahydrofuran was evoporated from the reaction mixture. Diluted hydrochloric acid was added to the residue. The acidic solution was extracted with ethyl acetate. The ertract was dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate=99:1→98:2→95:5) to give the title compound (128 g) having the following physical data:

Workup

  1. additionwas added dropwise into the mixture
  2. temperaturewith cooling in an ice-bath over 30 mins
  3. temperaturerefluxed at 8 hrs
  4. extractionThe acidic solution was extracted with ethyl acetate
  5. dry with materialThe ertract was dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate=99:1→98:2→95:5)

Sources & evidence

ORD record
ord-02f7f57adbba481e8ca06a2baf486f93
Source dataset
uspto-grants-1991_08
Patent number
US05037852

Reaction notes

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