6-Ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman → 3-[3-(8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acrylic acid ethyl ester

HRID 1869870Notes

Reaction equation

HRID 1869870 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=1)[O:9][C:8]([CH3:17])([CH3:16])[CH2:7][C:6]2([CH3:19])[CH3:18])#[CH:2].[CH2:20]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](I)[CH:27]=1)[CH3:21]>[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(N(CC)CC)C>[CH2:20]([O:22][C:23](=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[C:11]([CH:13]([CH3:14])[CH3:15])[CH:12]=2)[O:9][C:8]([CH3:17])([CH3:16])[CH2:7][C:6]3([CH3:18])[CH3:19])[CH:27]=1)[CH3:21]

Participants

6

Reactant 2

HCID 211072306-Ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman2×HCID 545009022-Propenoic acid, 3-(3-iodophenyl)-, ethyl ester

Product 1

HCID 690717073-[3-(8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Following General Procedure B and using 6-ethynyl-8-isopropyl-2,2,4,4-tetramethylchroman (Intermediate 32, 0.05 g, 0.2 mmol), ethyl-3-iodo cinnamate (Reagent 6, 0.118 g, 0.39 mmol), triethyl amine (2 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.107 mmol) followed by flash column chromatography over silica gel (230-400 mesh), the title compound was obtained (0.058 g, 69%).

Sources & evidence

ORD record
ord-6b2dfe8bbfc44d82a1c36844387cfb61
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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