Triphenylphosphine → HCID 66789913, compound

HRID 1510132Notes

Reaction equation

HRID 1510132 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:12]1([CH:15](O)[CH3:16])[CH2:14][CH2:13]1.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>[CH:12]1([CH:15]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH3:16])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 791041-CyclopropylethanolHCID 88068Methyl 3-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 66789913HCID 66789913, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-hydroxybenzoate (10.0 g, 65.7 mmol) in toluene (65.7 ml) was cooled to 0° C. and added 1-cyclopropylethanol (6.43 ml, 65.7 mmol), triphenylphosphine (18.9 g, 72.3 mmol), and DIAD (14.1 ml, 72.3 mmol). The reaction warmed to rt for sixteen hours. The reaction mixture was filtered through a fritted funnel to remove precipitated triphenylphosphine oxide and washed with toluene. The filtrate was concentrated. The residue was purified by column chromatography on silica gel Biotage 65i, eluting with 10% ethyl acetate/hexanes to give a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through a fritted funnel
  2. customto remove
  3. customprecipitated triphenylphosphine oxide
  4. washwashed with toluene
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by column chromatography on silica gel Biotage 65i
  7. washeluting with 10% ethyl acetate/hexanes
  8. customto give a colorless oil

Sources & evidence

ORD record
ord-df98797003da439ebeb9a1a433bdbbc4
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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