Triphenylphosphine → 4-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-7-carbaldehyde

HRID 2215197Notes

Reaction equation

HRID 2215197 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:23]2[CH:22]=[CH:21][S:20][C:19]=2[C:18]([CH:24]=[O:25])=[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:23]3[CH:22]=[CH:21][S:20][C:19]=3[C:18]([CH:24]=[O:25])=[CH:17][CH:16]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 111829574-Hydroxy-benzo[b]thiophene-7-carboxaldehydeHCID 115792322-(2-Tert-butyl-5-methyl-oxazol-4-yl)-ethanol

Product 1

HCID 219496634-[2-(2-tert-Butyl-5-methyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-7-carbaldehydeYield 47.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.800 g of the above prepared (example 1, step f]) 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 0.778 g of 4-hydroxy-benzo[b]thiophene-7-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, produced finally 0.713 g of the title compound as off-white crystals of mp. 140–42° (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-54aaed913ab3475ea9a329ac214ea9a4
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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