Iodo benzene diacetate → 3-Quinolin-6-ylbutanal

HRID 500231Notes

Reaction equation

HRID 500231 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-43c817df0d214acba7a8a27bc37b3265
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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