Ethyl 6-bromohexanoate → HCID 15790320, compound

HRID 346242Notes

Reaction equation

HRID 346242 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]Br)[CH3:2].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:16]1[C:12](=[O:22])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 117544Ethyl 6-bromohexanoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 15790320HCID 15790320, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure used to prepare 1,3-dihydro-1,3-dioxo-2H-isoindoleoctanoic acid ethyl ester. Thus, a mixture of 62.3 g (0.265 mole) of 6-bromohexanoic acid ethyl ester (ethyl 6-bromocapronate, 95%, Fluka) and 52.4 g (0.277 mole) of potassium phthalimide (98%, Aldrich) in 200 mL of dimethylformamide gave 67 g (87%) of crude title compound as a viscous oil. A 2.0 g sample of this oil was purified by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:10; flow rate 200 mL/min). Fractions containing title compound were combined and the solvents evaporated under reduced pressure to give 1.9 g (95% recovery) of colorless liquid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b4d84b354a864c6d9020abee6ff29b83
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

Loading…