Tetrahydrofuran → HCID 72732177, compound

HRID 1612983Notes

Reaction equation

HRID 1612983 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.O1CC[CH2:33][CH2:32]1>>[CH2:3]([O:5][C:6](=[O:7])[CH:8]=[C:32]([C:28]1[CH:27]=[CH:26][C:25]([CH2:23][CH2:22][CH2:20][CH2:19][CH3:18])=[CH:30][CH:29]=1)[CH3:33])[CH3:4]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 53817625HCID 53817625, compound

Product 1

HCID 72732177HCID 72732177, compound

Procedure

Sodium hydride (28.6 g, 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 room temperature and then refluxed at 8 hrs. Tetrahydrofuran was evaporated from the reaction mixture. Dilute hydrochloric acid was added to the residue. The acidic solution was extracted with ethyl acetate. The extract 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. customTetrahydrofuran was evaporated from the reaction mixture
  5. additionDilute hydrochloric acid was added to the residue
  6. extractionThe acidic solution was extracted with ethyl acetate
  7. dry with materialThe extract dried over magnesium sulfate
  8. customevaporated
  9. 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-75e9326a2d894895bcd08b1aedc7aadd
Source dataset
uspto-grants-1993_03
Patent number
US05191113

Reaction notes

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