Triphenylphosphine → HCID 19420788, compound

HRID 863860Notes

Reaction equation

HRID 863860 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.O[CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)(=O)C.C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:18][CH2:19][N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 27855874-(Benzo[d]oxazol-2-yl)phenol

Product 1

HCID 19420788HCID 19420788, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(benzoxazol-2-yl)phenol (0.3 g; 1.4 mmol), N-(2-hydroxyethyl)phthalimide (0.27 g; 1.4 mmol), triphenylphosphine (0.56 g; 2.1 mmol) and THF (5 ml) is added diisopropyl azodicarboxylate (0.42 ml; 2.1 mmol). The reaction is stirred 24 hours, diluted with ethyl acetate, washed with H2O, 2N HCl, NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by gradient elution column chromatography using CH2Cl2 and 1% MeOH/99% CH2Cl2 to yield N-[2-[4-(benzoxazol-2-yl)phenoxy]ethyl]phthalimide which is used directly in Step D.

Workup

  1. washwashed with H2O, 2N HCl, NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue is purified by gradient elution column chromatography

Sources & evidence

ORD record
ord-147052e3a30548f5b01d48130a3a099b
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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