Triethylamine → [4-(8-Ethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl) phenyl]acetic acid methyl ester

HRID 51691Notes

Reaction equation

HRID 51691 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:17]#[CH:18])[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])[CH3:2].[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1.C(N(CC)CC)C>[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.O1CCCC1>[CH3:19][O:20][C:21](=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:18]#[C:17][C:5]2[CH:6]=[C:7]3[C:12](=[C:3]([CH2:1][CH3:2])[CH:4]=2)[O:11][C:10]([CH3:13])([CH3:14])[CH2:9][C:8]3([CH3:16])[CH3:15])=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10378700Methyl 4-Iodophenylacetate2×HCID 225690198-Ethyl-6-ethynyl-2,2,4,4-tetramethylchroman2×

Product 1

HCID 69548054[4-(8-Ethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl) phenyl]acetic acid methyl ester

Reagents, catalysts & solvents 3

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

Procedure

Following general procedure F and using 8-ethyl-6-ethynyl-2,2,4,4-tetramethylchroman (Intermediate 48, 0.033 g, 0.136 mmol),methyl-4-iodo phenyl acetate (Reagent B, 0.034 g, 0.12 mmol), triethyl amine (2 mL), tetrahydrofuran (2 mL), copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol) the title compound was obtained (0.035 g, 73%).

Sources & evidence

ORD record
ord-e1fbf06b34fe46dbaa8ed7c3e5ae63c5
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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