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Tetrahydrofuran → [2-Fluoro-4-(2,2,4,4-tetramethyl-chroman-6-ylethynyl) phenyl]acetic acid ethyl ester

HRID 51659
Notes
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Reaction equation

HRID 51659 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]2([CH3:16])[CH3:15])#[CH:2].[CH2:17]([O:19][C:20](=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][C:23]=1[F:29])[CH3:18].C(N(CC)CC)C.O1CCCC1>CCCCCC.[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(OCC)(=O)C>[CH2:17]([O:19][C:20](=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]3([CH3:16])[CH3:15])=[CH:24][C:23]=1[F:29])[CH3:18]
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 156611382,2,4,4-Tetramethyl-6-ethynylchromanHCID 18740710Ethyl 2-fluoro-4-iodophenylacetate2×

Product 1

HCID 69548829[2-Fluoro-4-(2,2,4,4-tetramethyl-chroman-6-ylethynyl) phenyl]acetic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (0.204 g, 0.95 mmol), ethyl-2-fluoro-4-iodo phenyl acetate (Reagent C, 0.263 g, 0.86 mmol), triethyl amine, tetrahydrofuran, copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.075 g, 0.11 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.21 g, 62%).

Sources & evidence

ORD record
ord-9c9e5743ba70417798c464df3f2ebcf6
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06713647B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes