Water → HCID 69590709, compound

HRID 1744772Notes

Reaction equation

HRID 1744772 reaction equation
[H-].[Na+].[CH:3]12[CH2:9][C:8](=O)[CH:7]1[CH2:6][CH:5]=[CH:4]2.[OH2:11].[O:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH:3]12[CH2:9][C:8](=[CH:14][C:13]([O:12][CH2:16][CH3:15])=[O:11])[CH:7]1[CH2:6][CH:5]=[CH:4]2

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 297183Bicyclo[3.2.0]hept-2-en-6-one

Product 1

HCID 69590709HCID 69590709, compound

Procedure

A solution of triethylphosphonoacetate (10.7 g; 48 mmol) in tetrahydrofuran (5 ml) was added to a suspension of 60% sodium hydride dispersion (1.91 g; 48 mmol) in tetrahydrofuran (30 ml) maintaining the temperature between 5–15° C. A solution of bicyclo[3.2.0]hept-2-en-6-one (5 g; 46 mmol) in tetrahydrofuran (5 ml) was added maintaining the temperature between 5–15° C. The reaction mixture was stirred at ambient temperature for 30 minutes then demineralised water (30 ml) added. The phases are separated and toluene (20 ml) was added to the organic layer which was washed with demineralised water (2×20 ml). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a oil (7.74 g).

Workup

  1. temperaturemaintaining the temperature between 5–15° C
  2. temperaturemaintaining the temperature between 5–15° C
  3. additionadded
  4. customThe phases are separated
  5. additiontoluene (20 ml) was added to the organic layer which
  6. washwas washed with demineralised water (2×20 ml)
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab73323c343b44ab909f3bcf6c63efb0
Source dataset
uspto-grants-2006_03
Patent number
US07018818B2

Reaction notes

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