Diisopropylamine → methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-[4-[4-(hydroxymethyl)phenylethynyl]phenyl]allyloxy]-2-methyl-phenoxy]acetate

HRID 549900

Reaction equation

HRID 549900 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1)#[CH:2].C(NC(C)C)(C)C.[C:18]([C:22]1[CH:27]=[CH:26][C:25](/[C:28](/[C:45]2[CH:50]=[CH:49][C:48](I)=[CH:47][CH:46]=2)=[CH:29]/[CH2:30][O:31][C:32]2[CH:43]=[CH:42][C:35]([O:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[C:34]([CH3:44])[CH:33]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([C:22]1[CH:23]=[CH:24][C:25](/[C:28](/[C:45]2[CH:50]=[CH:49][C:48]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=3)=[CH:47][CH:46]=2)=[CH:29]/[CH2:30][O:31][C:32]2[CH:43]=[CH:42][C:35]([O:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[C:34]([CH3:44])[CH:33]=2)=[CH:26][CH:27]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 11170993(4-Ethynylphenyl)methanolHCID 86629308methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]acetate

Product 1

HCID 86629323methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-[4-[4-(hydroxymethyl)phenylethynyl]phenyl]allyloxy]-2-methyl-phenoxy]acetate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Ethynyl-4-(hydroxymethyl)benzene (169 mg, 1.28 mmol) and diisopropylamine (0.40 mL, 2.85 mmol) were added to a solution of methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]acetate (364 mg, 0.638 mmol; prepared as described in example 30) in tetrahydrofuran (10 mL). The mixture was degassed and copper(I) iodide (10 mg, 0.053 mmol) and bis(triphenylphosphine)palladium(II) dichloride (22 mg, 0.031 mmol) were added. The reaction mixture was stirred at ambient temperature overnight, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane/methanol 99:1) yielding methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-[4-[4-(hydroxymethyl)phenylethynyl]phenyl]allyloxy]-2-methylphenoxy]acetate as brown oil.

Workup

  1. customThe mixture was degassed
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel Fluka 60, dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-989692f9e56741d09f63b24c084d254a
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Linked notes

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