Triphenylphosphine → 4-{3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalene-1-carbaldehyde

HRID 479144

Reaction equation

HRID 479144 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH3:18])=[C:12]([CH2:14][CH2:15][CH2:16][OH:17])[N:13]=2)=[CH:5][CH:4]=1.O[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=[O:31])=[CH:22][CH:21]=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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([CH3:18])=[C:12]([CH2:14][CH2:15][CH2:16][O:17][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([CH:30]=[O:31])=[CH:22][CH:21]=3)[N:13]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 180035253-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1-ol

Product 1

HCID 180035974-{3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

g of the above prepared 3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1ol (4.04 mmol) was dissolved in 21 ml of toluene and treated successively at 0° C. with 0.696 g of 4-hydroxy-naphthalene-1-carbaldehyde (4.04 mmol), 1.061 g of triphenylphosphine (4.04 mmol), and 0.818 g (4.04 mmol) of DIAD. The cooling bath was then removed and stirring continued for 3 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with 3N NaOH and water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=7/3) left finally 1.084 g of the title compound as light yellow gum.

Workup

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with 3N NaOH and water
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  6. waitleft finally 1.084 g of the title compound as light yellow gum

Sources & evidence

ORD record
ord-744c70bc541d45089c2e43a675e97ae7
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Linked notes

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