Triphenylphosphine → (5-Ethyl-furan-2-yl)methyl 4-(5-undecyl-pyrimidin-2-yl)phenyl ether

HRID 1826550Notes

Reaction equation

HRID 1826550 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C1C=NC(C2C=CC(O)=CC=2)=NC=1)CCCCCCCCCC.[CH2:56]([C:58]1[O:62][C:61]([C:63]([O:65][C:66]2[CH:71]=[CH:70][C:69]([C:72]3[N:77]=[CH:76][C:75]([CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88])=[CH:74][N:73]=3)=[CH:68][CH:67]=2)=O)=[CH:60][CH:59]=1)[CH3:57]>C1COCC1>[CH2:78]([C:75]1[CH:74]=[N:73][C:72]([C:69]2[CH:70]=[CH:71][C:66]([O:65][CH2:63][C:61]3[O:62][C:58]([CH2:56][CH3:57])=[CH:59][CH:60]=3)=[CH:67][CH:68]=2)=[N:77][CH:76]=1)[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH3:88]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 155149814-(5-Undecyl-pyrimidin-2-yl)phenyl 5-ethyl-furan-2-carboxylateHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenol

Product 1

HCID 22134218(5-Ethyl-furan-2-yl)methyl 4-(5-undecyl-pyrimidin-2-yl)phenyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A fully reacted mixture of equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in THF is admixed with equimolar amounts of 4.9 g of 4-(5-undecyl-pyrimidin-2-yl)phenol and 5-ethyl-furan-2-yl-methanol (prepared by LiAlH4 reduction of methyl 5-ethyl-furan-2-carboxylate, which in turn can be obtained by esterification of 5-ethyl-furan-2-carboxylic acid from Example 1). The mixture is stirred for 24 h at room temperature and then evaporated to dryness under reduced pressure. Purification by chromatography (silica gel, dichloromethane) and recrystallization affords the target compound.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customPurification
  3. customby chromatography (silica gel, dichloromethane) and recrystallization
  4. customaffords the target compound

Sources & evidence

ORD record
ord-90567347dd314ee4bb7f8c8947acdd5f
Source dataset
uspto-grants-2006_05
Patent number
US07052742B1

Reaction notes

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