Iodo benzene diacetate → 3-Quinolin-6-ylbutanal

HRID 1257887Notes

Reaction equation

HRID 1257887 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:15])[CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH3:15])[CH2:12][CH:13]=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12217721Iodo benzene diacetateHCID 67223946HCID 67223946, compound

Product 1

HCID 866215133-Quinolin-6-ylbutanalYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-quinolin-6-ylbutan-1-ol (0.060 g, 0.30 mmol) in methylene chloride (3.0 mL) was added 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (0.005 g, 0.03 mmol) and iodobenzene diacetate (0.10 g, 0.33 mmol). The reaction was stirred overnight at RT. The mixture was purified by chromatography on silica gel with EtOAc in hexanes (0-40%) to afford the desired product (0.050 g, 84%). LCMS: (M+H)=200.0.

Workup

  1. customThe mixture was purified by chromatography on silica gel with EtOAc in hexanes (0-40%)

Sources & evidence

ORD record
ord-cbaeaf0bb76b47bdbf14a6732bd41d8d
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

Loading…