Cesium carbonate → 4-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxy)-benzo[b]thiophene-7-carbaldehyde

HRID 2215200Notes

Reaction equation

HRID 2215200 reaction equation
[C:1]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10]Cl)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH:13][C:14]1[C:22]2[CH:21]=[CH:20][S:19][C:18]=2[C:17]([CH:23]=[O:24])=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:1]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][O:13][C:14]2[C:22]3[CH:21]=[CH:20][S:19][C:18]=3[C:17]([CH:23]=[O:24])=[CH:16][CH:15]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111829574-Hydroxy-benzo[b]thiophene-7-carboxaldehydeHCID 219495892-Tert-butyl-4-chloromethyl-5-methyl-oxazole

Product 1

HCID 219496234-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxy)-benzo[b]thiophene-7-carbaldehydeYield 85.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.600 g of 2-tert-butyl-4-chloromethyl-5-methyl-oxazole (example 1, step b], 3.197 mmol) was dissolved in 12 ml of acetone and treated successively with 0.570 g of 4-hydroxy-benzo[b]thiophene-7-carbaldehyde (3.197 mmol), 1.146 g of Cs2CO3 (3.517 mmol), and 0.0265 g of KI (0.16 mmol). The mixture was then refluxed under an atmosphere of Ar. After cooling, the reaction mixture was poured onto crashed ice, extracted twice with AcOEt, the organic layer washed with water, dried over magnesium sulfate, and the solvents removed i.V. Flash chromatography (SiO2, hexane/AcOEt=8/2) yielded 0.901 g of the title compound as white crystals of mp. 119–200.

Workup

  1. temperatureThe mixture was then refluxed under an atmosphere of Ar
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured
  4. extractionextracted twice with AcOEt
  5. washthe organic layer washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvents removed i.V

Sources & evidence

ORD record
ord-08363a66de464f58b7e07f143cbbea34
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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