Carbon Dioxide → HCID 21292354, compound

HRID 623172Notes

Reaction equation

HRID 623172 reaction equation
O[C:2]1([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]([CH2:8][CH2:9][C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH2:6][C:5](=[O:16])[CH:4]=[CH:3]1.[CH3:25][CH2:26][O:27]CC.C(=O)(O)[O-].[Na+].C(=O)=O>C(OC(=O)C)(=O)C>[C:26]([O:16][C:5]1[CH:4]=[CH:3][C:2]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:7]([CH2:8][CH2:9][C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:6]=1)(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 516892Sodium Bicarbonate2×HCID 21292348HCID 21292348, compound

Product 1

HCID 21292354HCID 21292354, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

4-Hydroxy-5-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-4-(phenylethynyl)-2-cyclohexen-1-one (3.0 g, 9.2 mmole, prepared in a manner similar to that in Example 7b) was dissolved in acetic anhydride (25 mL) and stirred at RT under argon. After stirring 5 hr at RT, the reaction mixture was heated to reflux overnight. The reaction mixture was cooled to RT, poured into about 100 mL of ether, about 200 mL of saturated sodium bicarbonate added and the solution stirred. After evolution of CO2 was complete, solid sodium bicarbonate was added cautiously until foaming ceased. The layers were separated, the aqueous layer extracted twice with 100 mL portions of ether, the ether layers combined, washed with two 100 mL portions of sodium bicarbonate solution, two 100 mL portions of ether, the ether layers combined, washed with two 100 mL portions of saturated sodium bicarbonate solution, two 100 mL portions of water and 75 mL of saturated brine. After drying over anhydrous sodium sulfate, the organic layer was filtered and concentrated in vacuo to give 3.2 g of the title compound, a dark orange oil.

Workup

  1. stirringAfter stirring 5 hr at RT
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction mixture was cooled to RT
  5. additionadded
  6. stirringthe solution stirred
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted twice with 100 mL portions of ether
  9. washwashed with two 100 mL portions of sodium bicarbonate solution, two 100 mL portions of ether
  10. washwashed with two 100 mL portions of saturated sodium bicarbonate solution, two 100 mL portions of water and 75 mL of saturated brine
  11. dry with materialAfter drying over anhydrous sodium sulfate
  12. filtrationthe organic layer was filtered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eab4758b78084c24acb0e9323a674bd7
Source dataset
uspto-grants-1988_09
Patent number
US04772755

Reaction notes

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