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

HRID 278691Notes

Reaction equation

HRID 278691 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-9d1a5190d2dc43f183c4019e79110fbf
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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