Triphenylphosphine → HCID 69652314, compound

HRID 967485Notes

Reaction equation

HRID 967485 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([OH:11])[CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]O)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([O:11][CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74647p-Chlorophenethylic alcoholHCID 5462977Diethyl azodicarboxylateHCID 11819787Methyl 4-chloro-3-hydroxybenzoate

Product 1

HCID 69652314HCID 69652314, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

g (5.36 mmol) of 4-Chloro-3-hydroxy-benzoic acid methyl ester was dissolved in 40 ml of anhydrous tetrahydrofuran. To this solution was added 0.923 g (5.9 mmol) of 2-(4-chloro-phenyl)-ethanol, 5.35 g (equivalent to 16.1 mmol PPh3) of triphenylphosphine derivatized polystyrene and 2.80 g (16.1 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 (1/5). Yield 1.6 g. LC-MS (ES+): m/e=325 (M)+

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 (1/5)

Sources & evidence

ORD record
ord-9197bb0f980240dcb069db6298e7d5f0
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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