Triethylamine → (4-Methoxymethoxy-phenylethynyl)-trimethylsilane

HRID 2305607Notes

Reaction equation

HRID 2305607 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>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.O.C(OCC)(=O)C>[CH3:19][Si:20]([CH3:22])([CH3:21])[C:23]#[C:24][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110327301-Iodo-4-(methoxymethoxy)benzene

Product 1

HCID 10657368(4-Methoxymethoxy-phenylethynyl)-trimethylsilane

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 22728543Water ethylacetateSolvent

Procedure

5.74 g (21.7 mmol) of 1-iodo-4-methoxymethoxybenzene, 100 ml of triethylamine and a mixture of 1.53 g (2.18 mmol) of dichlorobis(triphenylphosphine)palladium and 831 mg (4.37 mmol) of copper iodide are introduced into a three-necked flask. 6.14 ml (43.5 mmol) of trimethylsilylacetylene are then added and the medium is stirred for 48 h at room temperature. It is then poured into a water/ethyl acetate mixture. The organic phase is washed twice with water and, after separation of the phases by settling, it is washed with magnesium sulphate and concentrated.

Workup

  1. additionare introduced into a three-necked flask
  2. washThe organic phase is washed twice with water
  3. customafter separation of the phases
  4. washit is washed with magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-107dc54a56b3407990ed501fdd2fb309
Source dataset
uspto-grants-2002_08
Patent number
US06441010B2

Reaction notes

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