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Triethylamine → 3-tert-Butyl-2-isopropoxy-6-methyl-5-trimethylsilanylethynyl-benzaldehyde

HRID 1869990
Notes
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Reaction equation

HRID 1869990 reaction equation
Br[C:2]1[C:3]([CH3:18])=[C:4]([C:7]([O:14][CH:15]([CH3:17])[CH3:16])=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].C(N(CC)CC)C.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].C(OCC)(=O)C>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:10]([C:8]1[C:7]([O:14][CH:15]([CH3:17])[CH3:16])=[C:4]([C:3]([CH3:18])=[C:2]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[CH:9]=1)[CH:5]=[O:6])([CH3:13])([CH3:12])[CH3:11]
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 211071513-Bromo-5-tert-butyl-6-isopropoxy-2-methyl-benzaldehyde2×

Product 1

HCID 211071563-tert-Butyl-2-isopropoxy-6-methyl-5-trimethylsilanylethynyl-benzaldehyde

Reagents, catalysts & solvents 3

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

Procedure

Following General Procedure D and using 3-bromo-5-tert-butyl-6-isopropoxy-2-methyl-benzaldehyde (Intermediate 141, 0.43 g, 1.37 mmol), triethyl amine, copper(I)iodide (0.021 g, 0.11 mmol), trimethylsilyl acetylene (1 mL), and dichlorobis(triphenylphosphine)palladium(II) (0.077 g, 0.11 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 2% ethyl acetate in hexane as the eluent, the title compound was obtained (0.45 g, ˜100%).

Sources & evidence

ORD record
ord-0b21b1959d37428b9d94a5cef15ce683
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07638648B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes