Ethyl 2-(diethoxyphosphoryl)butanoate → HCID 68850618, compound

HRID 1826073Notes

Reaction equation

HRID 1826073 reaction equation
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][C:18](C)([O-])[CH3:19].[K+].[CH3:23][S:24][CH:25]([C:36]1[CH:41]=[C:40](C=O)[CH:39]=[CH:38][C:37]=1[O:44][CH3:45])[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>O1CCCC1>[CH3:23][S:24][CH:25]([C:36]1[CH:41]=[C:40]([C:3]2([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:2]=[CH:1][CH:17]=[CH:18][CH2:19]2)[CH:39]=[CH:38][C:37]=1[O:44][CH3:45])[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27]

Participants

5

Reactant 3

HCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 11759308HCID 11759308, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68850618HCID 68850618, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, triethyl 2-phosphonobutyrate (3.77 g, 14.9 mmol) was dissolved in dehydrated tetrahydrofuran (40 mL) and potassium tert-butoxide (1.68 g, 15.0 mmol) was added under stirring and cooling with ice. After completion of the addition, the mixture was stirred for 1 hour. Following this, benzyl 2-methylthio-2-(5-formyl-2-methoxyphenyl)acetate (4.49 g, 13.6 mmol) dissolved in dehydrated tetrahydrofuran (30 mL) was added and the mixture was stirred for 6 hours at room temperature. The reaction mixture was concentrated and ice water was added, which was made acidic with 1 mol/L hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The extracte was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v) to afford 4.55 g (78%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling with ice
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred for 1 hour
  4. additionwas added
  5. stirringthe mixture was stirred for 6 hours at room temperature
  6. concentrationThe reaction mixture was concentrated
  7. additionice water was added
  8. extractionThe reaction mixture was extracted with ethyl acetate
  9. washThe extracte was washed with water and brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v)

Sources & evidence

ORD record
ord-816c8cb23a9745988fe27dd59f50de8f
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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