Tetrahydrofuran → HCID 131728926, compound

HRID 551703Notes

Reaction equation

HRID 551703 reaction equation
O1CCCC1.COP([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(OC)=O.[H-].[Na+].[CH3:22][C:23]12[CH2:29][C:28](=O)[CH:27]1[CH:26]=[CH:25][CH2:24]2>O>[CH3:22][C@:23]12[CH2:29][C:28](=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:27]1[CH:26]=[CH:25][CH2:24]2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 14924167HCID 14924167, compound

Product 1

HCID 131728926HCID 131728926, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A tetrahydrofuran (15 mL) solution of tert-butyl dimethylphosphonoacetate (3.29 g, 14.7 mmol) was added dropwise at 0° C. over 5 minutes to a tetrahydrofuran (15 mL) suspension of sodium hydride (0.59 g, 63%, 15.5 mmol), and the mixture was stirred at 0° C. for 15 minutes. To this solution, a tetrahydrofuran (15 mL) solution of 1-methylbicyclo[3.2.0]hept-3-en-6-one (1.60 g, 13.1 mmol) was added dropwise at 0° C. over 10 minutes, and the mixture was stirred at room temperature for 4 hours. The mixture was treated with water, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a yellow oil substance (1.80 g, 62%).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. customto obtain the compound of interest as a yellow oil substance (1.80 g, 62%)

Sources & evidence

ORD record
ord-986e3063e52f437da94fcfbcafbf892b
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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