Ethyl anisate → HCID 21874054, compound

HRID 723998Notes

Reaction equation

HRID 723998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[CH3:9][O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:15]([C:14]2[CH:20]=[CH:21][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)=[O:16])[CH:3]=1

Participants

5

Reactant 3

HCID 60979Ethyl anisateHCID 5813924-Chloro-2-methylpyridineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 21874054HCID 21874054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a cold (0° C.) solution of 4-chloro-2-picoline (10 g, 78.4 mmol) and ethyl 4-methoxybenzoate (14.1 g, 78.4 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (157 mL, 1.0 M in tetrahydrofuran, 157 mmol) dropwise via a pressure equalizing funnel over half an hour. Upon complete addition, the ice bath was removed and the resulting solution was heated at 45° C. for 15 hours. The mixture was cooled to room temperature, and the solution was concentrated. Methanol was added to quench the reaction, resulting in the formation of a yellow precipitate. The precipitate was collected by filtration and dried to give the product as a mixture of enol and ketone tautomers. MS m/z 262 (M+1).

Workup

  1. customover half an hour
  2. additionUpon complete addition
  3. customthe ice bath was removed
  4. temperatureThe mixture was cooled to room temperature
  5. concentrationthe solution was concentrated
  6. additionMethanol was added
  7. customto quench
  8. customthe reaction
  9. customresulting in the formation of a yellow precipitate
  10. filtrationThe precipitate was collected by filtration
  11. customdried
  12. customto give the product

Sources & evidence

ORD record
ord-8158751891aa43319ab2d9f15e32c72a
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

Loading…