Ethyl Acetoacetate → HCID 13799829, compound

HRID 1906475Notes

Reaction equation

HRID 1906475 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16](OCC)(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19]>>[C:16]([O:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dione

Product 1

HCID 13799829HCID 13799829, compoundYield 54%

Procedure

A solution of 22.8 g (0.111 mol) of N-3-hydroxypropyl phthalimide and 14.46 g (0.111 mol) of ethyl acetoacetate was heated at 145°-150° C. for 12 hours. Ethanol was removed with nitrogen flow during the course of the reaction. The mixture was cooled to room temperature, dissolved in dichloromethane, and washed with brine. The separated organic phase was dried over magnesium sulfate, concentrated in vacuo, and distilled at 211°-219° C. (0.125 mm Hg) to yield 17.3 g (54%) of a white solid; m.p. 67°-71° C. NMR: (CDCl3) δ2.0 (2H,m), 2.2 (3H,s), 3.3 (2H,s), 3.7 (2H,t), 4.05 (2M,t), 7.62 (4H,d).

Workup

  1. customEthanol was removed with nitrogen flow during the course of the reaction
  2. dissolutiondissolved in dichloromethane
  3. washwashed with brine
  4. dry with materialThe separated organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationdistilled at 211°-219° C. (0.125 mm Hg)

Sources & evidence

ORD record
ord-23779a48c3634928ba0b06a009232d0a
Source dataset
uspto-grants-1987_03
Patent number
US04652573

Reaction notes

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