Dimethylformamide → HCID 59648590, compound

HRID 1025913Notes

Reaction equation

HRID 1025913 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].C1C[O:13][CH2:12]C1.CN(C)C=O>>[CH:12]([C:5]1[O:4][C:3]([C:7]([OH:9])=[O:8])=[C:2]([CH3:1])[CH:6]=1)=[O:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 781273-Methyl-2-furoic acid

Product 1

HCID 59648590HCID 59648590, compound

Conditions

Temperature
-70 °C

Procedure

3-Methyl furoic acid (10 g, 79 mmol) and THF (400 mL) n-butyl lithium (67 mL, 0.167 mol) were stirred at a rate sufficient to maintain −70° C. (approx. 1 drop per sec). min then dimethylformamide (30 g, 0.395 mol) was added all at once. The reaction temperature was maintained for an additional 3 hr. After this time the reaction was quenched with the addition of saturated ammonium chloride. The aqueous phase was acidified with 6 N HCl, after extraction and recrystallized from water Intermediate 6 was obtained.

Workup

  1. temperatureThe reaction temperature was maintained for an additional 3 hr
  2. customAfter this time the reaction was quenched with the addition of saturated ammonium chloride
  3. extractionafter extraction
  4. customrecrystallized from water Intermediate 6
  5. customwas obtained

Sources & evidence

ORD record
ord-90bda2cc71d54130b512e560ae74609b
Source dataset
uspto-grants-2014_05
Patent number
US08729110B1

Reaction notes

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