Ethyl Acetate → HCID 57424210, compound

HRID 1869830Notes

Reaction equation

HRID 1869830 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].[CH3:13][Si:14]([CH3:19])([CH3:18])[CH2:15][CH2:16]O.Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC>[CH3:13][Si:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][O:11][C:10](=[O:12])[CH2:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 180132-(Trimethylsilyl)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222403932-(2-Fluoro-4-iodophenyl)acetic acid

Product 1

HCID 57424210HCID 57424210, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-fluoro-4-iodo phenyl acetic acid (0.3 g, 1.07 mmol) and 2-(trimethylsilyl)ethanol (0.28 mL, 1.95 mmol) in anhydrous dichloromethane (5 mL) was treated with 4-(dimethylamino)pyridine (0.275 g, 2.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.37 g, 1.95 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then subjected to flash column chromatography using 5% ethyl acetate in hexane as the eluent to afford the title compound as a white solid (0.37 g, 91%).

Workup

  1. customthe resulting reaction mixture

Sources & evidence

ORD record
ord-013f12afd11e4f9590f4d18552c2f2d4
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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