Triphenylphosphine → HCID 19420788, compound

HRID 1734696Notes

Reaction equation

HRID 1734696 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-93e980d58509499bb66d824e7688867d
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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