Furfural → HCID 86709730, compound

HRID 1423286Notes

Reaction equation

HRID 1423286 reaction equation
C([Li])CCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[C:13](=[O:20])([O:17][CH2:18][CH3:19])OCC.[O:21]1C=CC=[C:22]1[CH:26]=[O:27].[O:28]1[CH2:32][CH2:31][CH2:30]C1>CCCCCC>[O:21]1[CH2:22][CH2:26][O:27][CH:19]1[CH2:18][O:17][C:13](=[O:20])[CH:30]=[CH:31][C:32]1[O:28][CH:12]=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 7362FurfuralHCID 7766Diethyl CarbonateHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 178418339Butyllithium

Product 1

HCID 86709730HCID 86709730, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

In the next step, n-butyllithium (2.15 equivalents) in hexane was cooled to −70° C. and diisopropylamine (2.25 equivalents) was added while keeping the temperature below −60° C. Compound 1″ (1 equivalent) dissolved in tetrahydrofuran (THF) was added over 30 min at −70° C. After 10 min, diethyl carbonate (1.05 equivalents) dissolved in THF was added over 30 min keeping the reaction temperature below −60° C. After stirring for one hour at −60° C., the reaction was allowed to warm to 15° C. and furan-2-carbaldehyde (1.3 equivalents) dissolved in THF was added. After stirring for 20 hrs at room temperature, the reaction was rotary evaporated to dryness to yield ethyl 2-((1,3-dioxolan2-yl)methyl-3-(furan-2-yl)acrylate, compound 5″. Crude compound 5″ was used directly in the next reaction.

Workup

  1. customthe temperature below −60° C
  2. additionwas added over 30 min at −70° C
  3. additionwas added over 30 min
  4. customthe reaction temperature below −60° C
  5. temperatureto warm to 15° C.
  6. additionwas added
  7. stirringAfter stirring for 20 hrs at room temperature
  8. customthe reaction was rotary evaporated to dryness

Sources & evidence

ORD record
ord-a8e448aa52fe48dc929b21cd0443c0c4
Source dataset
uspto-grants-2015_01
Patent number
US08927574B2

Reaction notes

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