Tetrahydrofuran → 4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl ester

HRID 381171Notes

Reaction equation

HRID 381171 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]#[CH:12])[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].C(O[C:23]1[CH:28]=[CH:27][C:26](I)=[C:25]([CH3:30])[C:24]=1[F:31])(=O)C.C(N(CC)CC)C.O1CCCC1.[C:44]([O:47][CH2:48]C)(=[O:46])C>CCCCCC.[Cu]I>[CH3:48][O:47][C:44](=[O:46])[CH2:30][C:25]1[CH:26]=[CH:27][C:28]([C:12]#[C:11][C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([O:17][CH3:18])=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=2)=[CH:23][C:24]=1[F:31]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 225688511,3-Di-tert-butyl-5-ethynyl-2-methoxy-benzene2×HCID 69548383Methyl-2-fluoro-4-iodo-phenyl acetate

Product 1

HCID 695488624-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure F and using 1,3-di-tert-butyl-5-ethynyl-2-methoxy-benzene (Intermediate 169, 0.087 g, 0.33 mmol), methyl-2-fluoro-4-iodo phenyl acetate (Reagent H, 0.088 g, 0.30 mmol), triethyl amine (5 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladiun(II) (0.06 g, 0.085 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound (0.122 g, 89%) was obtained.

Sources & evidence

ORD record
ord-d03a64bbc968404894898103cf9822fd
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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