Triphenylphosphine → 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-isopropoxy-benzoic Acid Ethyl Ester

HRID 1831815Notes

Reaction equation

HRID 1831815 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7]([OH:15])[CH:6]=1)[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([CH3:13])[CH3:14])=[C:7]([O:15][CH2:26][CH2:25][C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylateHCID 183193363-Hydroxy-4-isopropyloxybenzoic acid ethyl ester

Product 1

HCID 696522853-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-isopropoxy-benzoic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (6.69 mmol) of 3-Hydroxy-4-isopropoxy-benzoic acid ethyl ester was dissolved in 20 ml of anhydrous tetrahydrofuran. To this solution was added 1.4 g (7.36 mmol) of 2-(2,4-Dichlorophenyl)-ethanol, 6.7 g (equivalent to 20 mmol PPh3) of triphenylphosphine derivatized polystyrene and 3.5 g (20 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with ethyl acetate. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate and the solution was washed three times with water and twice with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6).

Workup

  1. filtrationThe polymer was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. washthe solution was washed three times with water
  5. dry with materialThe organic phase was dried with magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/6)

Sources & evidence

ORD record
ord-d373108c66aa44d39edc1b982c53822f
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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