Pyridine → HCID 23050454, compound

HRID 1651838Notes

Reaction equation

HRID 1651838 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[OH:11][CH2:12][C:13]#[C:14][C:15]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1)=[O:16].P([O-])([O-])([O-])=O>C(Cl)Cl>[C:1]([O:11][CH2:12][C:13]#[C:14][C:15](=[O:16])[C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1061PhosphateHCID 6367Acetyl chlorideHCID 23050496HCID 23050496, compound

Product 1

HCID 23050454HCID 23050454, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.815 g of acetyl chloride and 0.827 g of pyridine were added simultaneously to a solution of 2.0 g (7.99 mmol) of 4-hydroxy-1-(3,4,5-trimethoxyphenyl)-2-butyn-1-one in 20 ml of methylene chloride. The reaction mixture was stirred at 0° for 1 hour, whereupon it was treated with 30 ml of phosphate buffer (pH 6) and the aqueous phase was extracted twice with methylene chloride. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was recrystallized from ethyl acetate/hexane and there was obtained 3-(3,4,5-trimethoxy-benzoyl)-2-propynyl acetate of melting point 104°-105°.

Workup

  1. extractionthe aqueous phase was extracted twice with methylene chloride
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7be08d16adc846fd87120a5d5bed18b8
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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