Carbon Dioxide → HCID 19041739, compound

HRID 1684041Notes

Reaction equation

HRID 1684041 reaction equation
CN(CCN(C)C)C.C([Li])CCC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:24]2[O:29]CCCO2)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.[C:30](=[O:32])=[O:31].Cl>C1COCC1.C(OCC)C>[CH3:23][O:22][C:20]1[CH:19]=[C:18]([CH:24]=[O:29])[CH:17]=[C:16]([O:15][CH3:14])[C:21]=1[C:30]([OH:32])=[O:31]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 19041781HCID 19041781, compoundHCID 178418339Butyllithium

Product 1

HCID 19041739HCID 19041739, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Anhydrous TMEDA (2.05 ml, 13.62 mmole) and 90 ml dry THF was cooled to -78° C. under an argon atmosphere. n-Butyllithium (11.35 ml of a 1.20M soln.) was added and after 15 minutes, 2-(3,5-dimethoxyphenyl)-1,3-dioxane (44) (FIG. 23) (3.05 g, 13.62 mmole) predissolved in 50 ml dry THF was added. The reaction was warmed to 0° C. and was stirred at that temperature for an additional 60 minutes (the solution turned from a blood red color to a dark brown color). The aryl lithium solution was then poured onto solid carbon dioxide covered with anhydrous diethyl ether. A white precipitate formed immediately. When the reaction warmed to room temperature, 15 ml of 10% HCl was added and the reaction was stirred overnight. The product was then extracted into chloroform. The organic layer was dried over MgSO4, and concentrated in vacuo to a white solid (1.311 g, 46%). The solid can be recrystallized from hexane/ethyl acetate.

Workup

  1. addition) was added and after 15 minutes
  2. additionwas added
  3. customA white precipitate formed immediately
  4. temperatureWhen the reaction warmed to room temperature
  5. stirringthe reaction was stirred overnight
  6. extractionThe product was then extracted into chloroform
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo to a white solid (1.311 g, 46%)
  9. customThe solid can be recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-53e9d7a7f8154a1ba1b8ff882a6584f3
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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