Water → HCID 22616357, compound

HRID 842950Notes

Reaction equation

HRID 842950 reaction equation
[H-].[Na+].[C:3]([C:5]1([C:12]2[C:21]3[O:20][CH2:19][CH2:18][O:17][C:16]=3[C:15]([O:22][CH3:23])=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)#[N:4].[OH2:24]>C1COCC1>[C:3]([C:5]1([C:12]2[C:21]3[O:20][CH2:19][CH2:18][O:17][C:16]=3[C:15]([O:22][CH3:23])=[CH:14][CH:13]=2)[CH2:6][CH2:7][C:8](=[CH:15][C:16]([O:17][CH2:18][CH3:19])=[O:24])[CH2:9][CH2:10]1)#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 15480788HCID 15480788, compound

Product 1

HCID 22616357HCID 22616357, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triethyl phosphonoacetate (0.72 mL, 3.6 mmol) in THF (9.4 mL) was added 60% sodium hydride (0.15 g, 3.6 mmol) under ice-cooling. The mixture was stirred at room temperature for 15 minutes, Compound 1 (0.94 g, 3.3 mmol) obtained in Example 1 was added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Then, water was added under ice-cooling, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1) to give Compound 10 (1.4 g, 97%) as a white solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2c96d64b638f46179eac077ef49a1d48
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

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