Triphenylphosphine → HCID 66790614, compound

HRID 1510117Notes

Reaction equation

HRID 1510117 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[C@@H:10](O)([CH2:12][CH3:13])[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C@H:10]([CH3:11])[CH2:12][CH3:13])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 757903-Chloro-4-fluorophenolHCID 444683(+)-2-ButanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 66790614HCID 66790614, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 0° C. solution of 3-chloro-4-fluorophenol (2.10 g, 14.3 mmol) in toluene (14.3 ml) was added (S)-(+)-sec-butanol (1.39 ml, 15.0 mmol), triphenylphosphine (3.76 g, 14.3 mmol), and DIAD (3.06 ml, 15.76 mmol). The reaction warmed to rt overnight. The reaction mixture was filtered through a fritted funnel and washed with toluene. The filtrate was concentrated. The residue was diluted with EtOAc and washed with 1N NaOH. The aqueous phase was extracted with EtOAc (2 times). The combined organics were dried with MgSO4, filtered, and concentrated. The residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 4% EtOAc/hexanes) to give the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through a fritted funnel
  2. washwashed with toluene
  3. concentrationThe filtrate was concentrated
  4. additionThe residue was diluted with EtOAc
  5. washwashed with 1N NaOH
  6. extractionThe aqueous phase was extracted with EtOAc (2 times)
  7. dry with materialThe combined organics were dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 4% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dc6a76b9a85846e28ffcbe1afb1ddc71
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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