Diketene → HCID 14153228, compound

HRID 649002Notes

Reaction equation

HRID 649002 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[N:7]1([CH2:12][CH2:13][O:14][C:15]2[CH:27]=[CH:26][C:18]([C:19]([O:21][CH2:22][CH2:23][CH2:24][OH:25])=[O:20])=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=[CH:8]1>C(Cl)(Cl)Cl>[C:4]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][N:7]2[CH:11]=[CH:10][N:9]=[CH:8]2)=[CH:27][CH:26]=1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 14153225HCID 14153225, compound

Product 1

HCID 14153228HCID 14153228, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After adding at room temperature 4.1 ml of diketene dropwise to 10 g of 3-hydroxypropyl 4-[2-(1-imidazolyl)ethoxy]benzoate dissolved in 300 ml of chloroform, the resultant mixture was stirred for further 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 10.1 g of 3-[4-[2-(1-imidazolyl)ethoxy]benzoyloxy]propyl acetoacetate as colorless crystals (m.p. 49.5°-51.5° C.; yield: 78%)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-998beac7d6ed48d9891873c237f4f6d1
Source dataset
uspto-grants-1988_04
Patent number
US04737506

Reaction notes

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