Ethyl Acetoacetate → HCID 13799835, compound

HRID 1906480Notes

Reaction equation

HRID 1906480 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1.[C:13](OCC)(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>>[C:13]([O:1][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 122503792-(1,3-dihydro-2H-isoindol-2-yl)ethanol

Product 1

HCID 13799835HCID 13799835, compoundYield 22%

Procedure

A solution of 4.67 g (0.029 mol) of 2-(2-hydroxyethyl) isoindoline and 3.72 g (0.029 mol) of ethyl acetoacetate was heated at 100°-110° C. under nitrogen for 36 hours. Ethanol was removed with nitrogen flow during the course of the reaction. The mixture was subjected to flash chromatography (silica gel, 1:1 ethylacetate/petroleum ether) to give 1.54 g (22%) of a dark oil. NMR (CDCl3) δ 2.2 (3H, s), 2.94 (2H, t), 3.4 (2H, s). 3.9 (4H, s), 4.24 (2H, t), 7.04 (4H, s).

Workup

  1. customEthanol was removed with nitrogen flow during the course of the reaction

Sources & evidence

ORD record
ord-1f058486b46647759e420ae615869205
Source dataset
uspto-grants-1987_03
Patent number
US04652573

Reaction notes

Loading…