Ethyl orthoformate → HCID 66847930, compound

HRID 475428Notes

Reaction equation

HRID 475428 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3C=O)=[N:7][O:8][C:4]=2[CH:3]=1.[CH:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])OCC>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:19]([O:23][CH2:24][CH3:25])[O:26][CH2:27][CH3:28])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 866759952-(6-Bromobenzo[d]isoxazol-3-yl)benzaldehyde2×

Product 1

HCID 66847930HCID 66847930, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred suspension of 2-(6-bromobenzo[d]isoxazol-3-yl)benzaldehyde (Compound 4a) (10 g) in dry ethanol (100 mL) was added p-toluenesulfonic acid (0.315 g) followed by triethyl orthoformate (11.01 mL, 9.81 g). The suspension was stirred at 45° C. until a clear solution resulted and then maintained at 45° C. for 45 min. The solvent was removed under vacuum and then the mixture was diluted with ethyl acetate and then washed with saturated sodium carbonate solution, brine and then dried over anhydrous sodium sulfate, filtered and evaporated to give the title product (12.6 g).

Workup

  1. customresulted
  2. temperaturemaintained at 45° C. for 45 min
  3. customThe solvent was removed under vacuum
  4. additionthe mixture was diluted with ethyl acetate
  5. washwashed with saturated sodium carbonate solution, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-75172dc3bc1f4a749e9bfecad9efacab
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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