Triphenylphosphine → HCID 135725107, compound

HRID 993442Notes

Reaction equation

HRID 993442 reaction equation
O.Cl.[C:3]([C:7]1[CH:8]=[C:9]([C:18]2[O:19][CH:20]=[C:21]([CH2:23][CH2:24]OC3C=CC(CNCC)=CC=3)[N:22]=2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:6])([CH3:5])[CH3:4].C(C1C=C(C2OC=C(CCOC3C=CC(CNCC)=CC=3)N=2)C=C(C(C)(C)C)C=1O)(C)(C)C.Cl.[CH:70]([C:72]1[CH:73]=[C:74]([CH:77]=[CH:78][C:79]=1[OH:80])[CH:75]=[O:76])=[O:71].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:14]([C:11]1[CH:10]=[C:9]([C:18]2[O:19][CH:20]=[C:21]([CH2:23][CH2:24][O:80][C:79]3[CH:78]=[CH:77][C:74]([CH:75]=[O:76])=[CH:73][C:72]=3[CH:70]=[O:71])[N:22]=2)[CH:8]=[C:7]([C:3]([CH3:4])([CH3:5])[CH3:6])[C:12]=1[OH:13])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1651064-HydroxyisophthalaldehydeHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 137231698HCID 137231698, compound

Product 1

HCID 135725107HCID 135725107, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a flask, 4.75 g (15 mmole) of the compound of Example 1 C, 2.36 g (15.75 mmole) of 3-formyl-4-hydroxybenzaldehyde, and 3.93 g (15 mmole) of triphenylphosphine were dissolved in 45 ml tetrahydrofuran with stirring, under nitrogen. The solution was chilled to −10° and a solution of 2.36 ml (15 mmole) diethyl azodicarboxylate in 15 ml. Tetrahydrofuran was added over 10 minutes, with stirring. The reaction exothermed to +1° C. The bath was removed and the reaction stirred under nitrogen for 18 hours. The reaction was then stripped, dissolved in a minimum amount of methylene chloride and placed in the freezer. The diethoxycarbonylhydrazine was then filtered off and the filtrate was chromatographed, Prep 500, two columns, eluting with 0 to 20% ethyl acetate/toluene gradient over 30 minutes. The appropriate fractions were bulked and stripped to give 3.3 g (49%) product which was used without further purification.

Workup

  1. temperatureThe solution was chilled to −10°
  2. stirringwith stirring
  3. customexothermed to +1° C
  4. customThe bath was removed
  5. stirringthe reaction stirred under nitrogen for 18 hours
  6. dissolutiondissolved in a minimum amount of methylene chloride
  7. filtrationThe diethoxycarbonylhydrazine was then filtered off
  8. customthe filtrate was chromatographed
  9. washPrep 500, two columns, eluting with 0 to 20% ethyl acetate/toluene gradient over 30 minutes

Sources & evidence

ORD record
ord-ef620dcdf85e41bbacb261cace2a3425
Source dataset
uspto-grants-2002_10
Patent number
US06472387B1

Reaction notes

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