Triphenylphosphine → HCID 69652322, compound

HRID 967486Notes

Reaction equation

HRID 967486 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-accdcdaf1d0f491a88d097c2de092d30
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

Loading…