Triphenylphosphine → 5-[2-(2,4-Dichloro-phenyl)-ethoxy]-isophthalic acid dimethyl ester

HRID 967453Notes

Reaction equation

HRID 967453 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:34])[C:23]1[CH:32]=[C:31]([OH:33])[CH:30]=[C:25]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:47][C:48]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:49]=1[CH2:55][CH2:56]O>C1COCC1>[CH3:29][O:28][C:26](=[O:27])[C:25]1[CH:30]=[C:31]([O:33][CH2:56][CH2:55][C:49]2[CH:50]=[CH:51][C:52]([Cl:54])=[CH:53][C:48]=2[Cl:47])[CH:32]=[C:23]([C:22]([O:21][CH3:20])=[O:34])[CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 696522995-[2-(2,4-Dichloro-phenyl)-ethoxy]-isophthalic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
5 °C

Procedure

1.75 g of triphenylphosphine and 1 g of 5-Hydroxy-isophthalic acid dimethyl ester were dissolved in 17 ml of anhydrous THF. The solution was cooled to 0-10° C. and a solution of 1 ml DEAD in 1 ml anhydrous THF was added dropwise over 20 min. The reaction was warmed to RT and stirred for 45 min. A solution of 11.3 ml 2-(2,4-Dichlorophenyl)-ethanol in 1 ml anhydrous THF was added with cooling. The reaction was stirred at RT for 16 h, then the solvents were removed under reduced pressure. The residue was treated with n-hepane:ethyl acetate/1:1. The filtrate was dried under reduced pressure and the product was purified by silica gel chromatography, eluting with n-heptane:ethyl acetate/4:1 to n-heptane:ethyl acetate/3:1.

Workup

  1. temperatureThe reaction was warmed to RT
  2. temperaturewith cooling
  3. stirringThe reaction was stirred at RT for 16 h
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was treated with n-hepane
  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-e4509b19e49a44c8aa1f55e82a8152e9
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

Loading…