1,1,3,3-Tetramethylguanidine → HCID 67448165, compound

HRID 2368128Notes

Reaction equation

HRID 2368128 reaction equation
[C:1]([Si:5]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]#[CH:26])[CH2:21][CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH:27]1([CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35](I)=[C:36]([OH:38])[CH:37]=2)[CH2:29][CH2:28]1.CN(C)C(N(C)C)=N>CN(C=O)C.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.[Cu](I)I>[C:1]([Si:5]([O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]2[O:38][C:36]3[CH:37]=[C:32]([O:31][CH2:30][CH:27]4[CH2:28][CH2:29]4)[CH:33]=[CH:34][C:35]=3[CH:26]=2)[CH2:23][CH2:24]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 57517507HCID 57517507, compoundHCID 57517508HCID 57517508, compound

Product 1

HCID 67448165HCID 67448165, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl [(4-ethynylcyclohexyl)oxy]diphenylsilane (3.52 g), 5-(cyclopropylmethoxy)-2-iodophenol (2.82 g), bis(triphenylphosphine)palladium(II) dichloride (0.34 g), copper iodide (0.09 g) and 1,1,3,3-tetramethylguanidine (3.65 mL) in DMF (30 mL) was stirred at room temperature overnight under an argon atmosphere. The reaction mixture was extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (3.36 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate and water
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ca4e55ae51e942eb9869858d34f296d8
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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