Ethyl Acetoacetate → 6-Phthalimidohexyl acetoacetate

HRID 1762469

Reaction equation

HRID 1762469 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[C:19](OCC)(=[O:24])[CH2:20][C:21]([CH3:23])=[O:22]>>[C:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13])(=[O:24])[CH2:20][C:21]([CH3:23])=[O:22]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 129502192-(6-hydroxyhexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 137526576-Phthalimidohexyl acetoacetateYield 75%

Conditions

Temperature
145 °C

Procedure

A mixture of 22.1 g (0.09 mol) of N-(6-hydroxyhexyl) phthalimide and 10.2 g (0.08 mol) of ethyl acetoacetate was heated in an oil bath at 145° C. under nitrogen for 15 hours. After drying on high vacuum the residue was subjected to flash chromatography (silica gel, 7:3 petroleum ether/ether). The product was isolated as 12.9 g (75%) of a pale yellow oil b.p. 218°-226° C./0.15 mm. NMR: (CDCl3) w 1.5 (8H, m), 2.21 (3H, s), 3.35 (2H, s), 3.55 (2H, m), 3.99 (2H, t), 7.5 (4H, m).

Workup

  1. customAfter drying on high vacuum the residue

Sources & evidence

ORD record
ord-c2c342e43707401aa263e2b77dba49a2
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Linked notes

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