Acetone → HCID 54377171, compound

HRID 582800Notes

Reaction equation

HRID 582800 reaction equation
COC([C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([C:12]([O:14]C)=O)[N:6]=1)=O.[CH3:16][OH:17].[BH4-].[Na+].C[C:21]([CH3:23])=[O:22].[O:24]1CC[CH2:26][CH2:25]1>>[Br:11][C:9]1[CH:10]=[C:5]([CH2:16][O:17][C:25](=[O:24])[CH3:26])[N:6]=[C:7]([CH2:12][O:14][C:21](=[O:22])[CH3:23])[CH:8]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 11953411HCID 11953411, compound

Product 1

HCID 54377171HCID 54377171, compound

Conditions

Temperature
0 °C

Procedure

5 g of 4-bromopyridine-2,6-dicarboxylic acid dimethyl ester are dissolved in 175 ml of tetrahydrofuran at room temperature. Then 75 ml of methanol are added. The mixture is cooled to 0° C.; 3.44 g of sodium borohydride are added in portions over a period of 45 minutes and the mixture is allowed to rise to room temperature. After 1 hour 30 ml of acetone are added dropwise within a period of 10 minutes. The reaction mixture is heated under reflux for 1 hour. The reaction mixture is then concentrated to dryness using a rotary evaporator. The residue is stirred at room temperature into 50 ml of pyridine. 0.1 g of 4-dimethylaminopyridine is added thereto and the mixture is then cooled to 0° C. 34.4 ml of acetic anhydride are added dropwise within a period of 30 minutes. The suspension is allowed to rise to room temperature. 50 ml of tetrahydrofuran are added. After being stirred overnight at room temperature, the reaction mixture is filtered and washed twice using 50 ml of tetrahydrofuran each time. The filtrate is concentrated using a rotary evaporator. 4-Bromo-2,6-di(acetoxymethyl)pyridine is obtained by crystallisation (melting point: 66-69° C.).

Workup

  1. customto rise to room temperature
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 1 hour
  4. concentrationThe reaction mixture is then concentrated to dryness
  5. customa rotary evaporator
  6. addition0.1 g of 4-dimethylaminopyridine is added
  7. temperaturethe mixture is then cooled to 0° C
  8. addition34.4 ml of acetic anhydride are added dropwise within a period of 30 minutes
  9. customto rise to room temperature
  10. addition50 ml of tetrahydrofuran are added
  11. stirringAfter being stirred overnight at room temperature
  12. filtrationthe reaction mixture is filtered
  13. washwashed twice
  14. concentrationThe filtrate is concentrated
  15. customa rotary evaporator

Sources & evidence

ORD record
ord-be20d49967eb4ddabc83bad825dc261c
Source dataset
uspto-grants-1999_07
Patent number
US05925744

Reaction notes

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