3-Furaldehyde → (E)-3-styrylfuran

HRID 256557

Reaction equation

HRID 256557 reaction equation
CC(C)([O-])C.[K+].C(C1C=COC=1)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[PH4+].COC=C(C1SC=CC=1COC1C=CC=CC=1)C(OC)=O.[CH2:56]([C:63]1C=CS[C:64]=1[C:68](=[CH:73][O:74][CH3:75])C(OC)=O)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.CCOCC.O>[CH:63](/[C:64]1[CH:68]=[CH:73][O:74][CH:75]=1)=[CH:56]\[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

10

Reactant 6

HCID 103513-FuraldehydeHCID 13097Triphenylphosphine OxideHCID 5460504PhosphoniumHCID 23665647Potassium tert-butoxideHCID 54504656Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoateHCID 54572621Methyl 3-methoxy-2-(3-phenoxymethyl-2-thienyl)propenoate

Product 1

HCID 14326174(E)-3-styrylfuranYield 32.1%

Reagents, catalysts & solvents 3

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Potassium tert-butoxide (35.7 g) was added in one portion to a stirred suspension of benzyltriphenylphosphonium chloride (41.6 g) in ether (1 liter). After 1 hour, a solution of 3-formylfuran (17.5 g) in ether (60 ml) was added to the resulting orange mixture which was then stirred for 2 hours, poured into water, and extracted with ether. The extracts were washed with water, dried and concentrated to give a solid. Trituration of this solid with ether enabled much of the weakly-soluble triphenylphosphine oxide and excess phosphonium salt to be separated, and the ether-soluble fraction (37.06 g) was chromatographed using ether as eluent to give a mixture of (E)- and (Z)-isomers of 3-styrylfuran (27 g) as a yellow solid. Crystallisation twice from methanol gave (E)-3-styrylfuran (5.12 g), mp 96° C., as a yellow solid.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid
  6. customto be separated
  7. customthe ether-soluble fraction (37.06 g) was chromatographed
  8. customto give
  9. customCrystallisation twice from methanol

Sources & evidence

ORD record
ord-9f272b85516241a9987d72e581965f9a
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Linked notes

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