Furfural → HCID 67088637, compound

HRID 389080Notes

Reaction equation

HRID 389080 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(NC(C)C)(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][CH2:29]1>CCCCCC>[O:21]1[CH2:22][CH2:26][O:27][CH:4]1[CH2:3][C:2](=[CH:1][C:29]1[O:28][CH:32]=[CH:31][CH:30]=1)[C:13]([O:17][CH2:18][CH3:19])=[O:20]

Participants

7

Reactant 5

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

Product 1

HCID 67088637HCID 67088637, 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-ce5d3fb5222a41f5b656b436dfc4ba27
Source dataset
uspto-grants-2013_02
Patent number
US08378105B2

Reaction notes

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