Triethylamine → (4-Methoxymethoxy-phenylethynyl)-trimethylsilane

HRID 1532295Notes

Reaction equation

HRID 1532295 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]>[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

6

Reactant 3

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

Product 1

HCID 10657368(4-Methoxymethoxy-phenylethynyl)-trimethylsilane

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 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 dichloro-bis(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-197b43f766584c9f9ee37c3b99a696b4
Source dataset
uspto-grants-2001_03
Patent number
US06201019B1

Reaction notes

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