Ethyl orthoformate → HCID 118162409, compound

HRID 707525Notes

Reaction equation

HRID 707525 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](C=O)[CH:5]=[CH:4][C:3]=1[F:10].[CH:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])OCC>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[C:3]([F:10])=[CH:4][CH:5]=[C:6]([CH:11]([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[N:7]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 722128091211531-38-2

Product 1

HCID 118162409HCID 118162409, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 702EthanolSolvent

Procedure

To a mixed solution of a commercially available product of 6-chloro-5-fluoropyridine-2-carbaldehyde (820 mg, 5.14 mmol) and ethanol (10.0 mL) were added triethyl orthoformate (2.56 mL, 15.4 mmol) and pyridinium p-toluenesulfonate (64.6 mg, 0.257 mmol) at room temperature. The resultant mixture was stirred at 80° C. for 5 hours. The reaction mixture was concentrated under a reduced pressure, water was added to the residue, and the resultant solution was extracted with ethyl acetate two times. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, to give a crude product (977 mg) of the title compound. The product was used in the subsequent reaction without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resultant solution was extracted with ethyl acetate two times
  4. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-8d5104c210344dbcb3ee2593fc42fc4d
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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