Carbon Dioxide → HCID 22367127, compound

HRID 486925Notes

Reaction equation

HRID 486925 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:13][C:14]#[N:15])=[CH:9][C:4]=2[O:3][CH2:2]1.C([Li])CCC.[C:21](=[O:23])=[O:22].O>CCOCC.CCCCCC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH:13]([C:14]#[N:15])[C:21]([OH:23])=[O:22])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 22367135HCID 22367135, compoundHCID 178418339Butyllithium

Product 1

HCID 22367127HCID 22367127, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

5.0 g of [{2-(1,3-benzodioxol-5-yl)ethyl}thio]acetonitrile was dissolved in 50 ml of anhydrous ether. 22 ml of a 1.6M solution of n-butyllithium in hexane was added to the solution at -78° C. The mixture was stirred at -50° C. for 2 h. It was cooled again to -78° C. and 10 g of dry ice was added thereto. The temperature of the mixture was elevated to room temperature. Water was added to the reaction mixture. After extraction with chloroform, the extract was dried over magnesium sulfate and concentrated. The residue was purified according to silica gel column chromatography (chloroform) and recrystallized from ethyl acetate/hexane to obtain 0.70 g of the intended compound in the form of colorless needles.

Workup

  1. temperatureIt was cooled again to -78° C.
  2. customwas elevated to room temperature
  3. extractionAfter extraction with chloroform
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0ae89dacbaf647208f358b37af1bcc1d
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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