Triphenylphosphine → HCID 69652268, compound

HRID 1831781Notes

Reaction equation

HRID 1831781 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([I:29])=[C:25]([OH:30])[CH:24]=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:44][C:45]1[CH:50]=[C:49]([Cl:51])[CH:48]=[CH:47][C:46]=1[CH2:52][CH2:53]O>C1COCC1>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([I:29])=[C:25]([O:30][CH2:53][CH2:52][C:46]2[CH:47]=[CH:48][C:49]([Cl:51])=[CH:50][C:45]=2[Cl:44])[CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 69652268HCID 69652268, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

6.6 g of triphenylphosphine and 5 g of 4-Iodo-3-hydroxy-benzoic acid methyl ester were dissolved in 65 ml of anhydrous THF. The solution was cooled to 0° C. to 10° C. and a solution of 3.7 ml DEAD in 7.5 ml anhydrous THF was added dropwise over 20 min. The reaction was warmed to RT and stirred for 45 min. A solution of 2.8 ml 2-(2,4-Dichlorophenyl)-ethanol in 3 ml anhydrous THF was added with cooling. The reaction was stirred at RT for 3 h, then the solvents were removed under reduced pressure. The residue was treated with n-heptane:ethyl acetate/1:1. The filtrate was dried under reduced pressure. The product was purified by silica gel chromatography, eluting with n-heptane:ethyl acetate/4:1 to n-heptane:ethyl acetate/1:1.

Workup

  1. temperatureThe solution was cooled to 0° C. to 10° C.
  2. temperaturewith cooling
  3. stirringThe reaction was stirred at RT for 3 h
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was treated with n-heptane
  6. customThe filtrate was dried under reduced pressure
  7. customThe product was purified by silica gel chromatography
  8. washeluting with n-heptane

Sources & evidence

ORD record
ord-c1f29a903e4942c7aaad4d85268f428b
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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