Triphenylphosphine → 4-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalene-1-carbaldehyde

HRID 2215193Notes

Reaction equation

HRID 2215193 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=[O:26])=[CH:17][CH:16]=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>[C:1]([C:5]1[O:6][C:7]([CH3:13])=[C:8]([CH2:10][CH2:11][O:12][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]=[O:26])=[CH:17][CH:16]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 115792322-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanol

Product 1

HCID 116457474-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-naphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.800 g of the above prepared 2-(2-tert-butyl-5-methyl-oxazol-4-yl)-ethanol (4.37 mmol) was dissolved in 25 ml of toluene and treated successively at 0° C. with 0.752 g of 4-hydroxy-naphthalene-1-carbaldehyde (4.37 mmol), 1.145 g of triphenylphosphine (4.37 mmol), and 0.883 g (4.37 mmol) of DIAD. The cooling bath was then removed and stirring continued for 4 h. Pouring onto crashed ice, twofold extraction with EtOEt, washing with dil. NaOH and water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=6/4) and crystallization from EtOEt, delivered finally 0.791 g of the title compound as off-white crystals of mp. 155–57° (dec.).

Workup

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with EtOEt
  4. washwashing with dil. NaOH and water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  6. customfollowed by flash chromatography (SiO2, hexane/AcOEt=6/4) and crystallization from EtOEt

Sources & evidence

ORD record
ord-7b3c4f0d613c4b5a8f1cb100ab5a8a5e
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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