Triphenylphosphine → HCID 69652322, compound

HRID 1831825Notes

Reaction equation

HRID 1831825 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F: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]([F: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 120168924-Fluoro-3-hydroxy-benzoic acid methyl ester

Product 1

HCID 69652322HCID 69652322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g (2.94 mmol) of 4-Fluoro-3-hydroxy-benzoic acid methyl ester was dissolved in 30 ml of anhydrous tetrahydrofuran. To this solution was added 0.506 g (3.23 mmol) of 2-(4-chloro-phenyl)-ethanol, 2.93 g (equivalent to 8.8 mmol PPh3) of triphenylphosphine derivatized polystyrene and 1.53 g (8.8 mmol) of DEAD. The solution was shaken for 16 h at RT. The polymer was filtered off and washed with tetrahydrofuran. The solvent was removed under reduced pressure. The residue was taken-up in ethyl acetate/n-heptane (1/5) and the insoluble residue was removed by filtration. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5).

Workup

  1. filtrationThe polymer was filtered off
  2. washwashed with tetrahydrofuran
  3. customThe solvent was removed under reduced pressure
  4. customthe insoluble residue was removed by filtration
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/5)

Sources & evidence

ORD record
ord-72e8c8b2a82d4990ae593339d96bb36d
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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