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Tetrahydrofuran → 6-(4-tert-Butoxycarbonylmethyl-phenylethynyl)-4,4,7-trimethyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid ethyl ester

HRID 1870033
Notes
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Reaction equation

HRID 1870033 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([C:17]#[C:18][Si](C)(C)C)=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:24])([CH3:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:43]1CCCC1.C1(N(C[C:54]2C=C(C#C[Si](C)(C)C)C=C3[C:63]=2[O:62][C:61]([CH3:65])([CH3:64])[CH2:60]C3(C)C)C)CC1.[CH3:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]>[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.C(N(CC)CC)C.O>[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([C:17]#[C:18][C:76]3[CH:75]=[CH:74][C:79]([CH2:54][C:63]([O:62][C:61]([CH3:65])([CH3:64])[CH3:60])=[O:43])=[CH:78][CH:77]=3)=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:24])([CH3:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 2724141Tetrabutylammonium FluorideHCID 690745094,4,7-Trimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester2×HCID 690745208-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-6-trimethylsilanylethynyl chroman2×

Product 1

HCID 690738306-(4-tert-Butoxycarbonylmethyl-phenylethynyl)-4,4,7-trimethyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4,4,7-Trimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester (Intermediate 193, 0.26 g, 0.76 mmol) was treated with a 1M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (3 mL, 3 mmol) under argon and the resulting reaction mixture was stirred at ambient temperature for 1 h. Water was added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was used as such for the next step. Following General Procedure B and using the oil (0.76 mmol), 4-iodo-tert-butyl phenyl acetate (Reagent 10, 0.23 g, 0.72 mmol), triethyl amine (2 mL), copper(I)iodide (0.06 g, 0.32 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (0.14 g, 0.2 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 12% ethyl acetate in hexane as the eluent, the title compound was obtained as a viscous, pale yellow oil (0.23 g, 66%).

Workup

  1. customthe resulting reaction mixture
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil that

Sources & evidence

ORD record
ord-60bb94fef25e4da39454b9fb9e833129
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07638648B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes