Water → 4-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether

HRID 1071331Notes

Reaction equation

HRID 1071331 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29].C(N(CC)CC)C.O>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.CCOCC>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 14903624Silane, [(4-bromophenyl)methoxy](1,1-dimethylethyl)diphenyl-2×

Product 1

HCID 102971754-[(trimethylsilyl)ethynyl]benzyl tert-butyldiphenylsilyl Ether

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A 25 mL round bottom flask was flame-dried under high vacuum. The vacuum was broken by the addition of dry argon, and the flask was allowed to cool to room temperature. The flask was charged with 2.0 g (4.70 mmol) of 4-bromobenzyl tert-butyldiphenylsilyl ether (Compound 1), 2.0 mL (14.1 mmol) of (trimethylsilyl)acetylene, and 16.5 mL of triethylamine. The solution was purged with argon for 15 minutes and bis(triphenylphosphine)palladium (II) chloride (83 mg, 0.12 mmol) and copper (I) iodide (22 mg, 0.12 mmol) were added and the solution stirred at ambient temperature for 3 days. The solution was poured into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted 3 times with ether. The combined ether layers were washed once with brine, and dried over magnesium sulfate, and the solvents were removed under reduced pressure. The residue was purified by distillation (bp=180° B 185° C., 1 torr) to give the title compound.

Workup

  1. customA 25 mL round bottom flask was flame-dried under high vacuum
  2. additionThe vacuum was broken by the addition of dry argon
  3. customThe solution was purged with argon for 15 minutes
  4. additionThe solution was poured into a separatory funnel
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted 3 times with ether
  7. washThe combined ether layers were washed once with brine
  8. dry with materialdried over magnesium sulfate
  9. customthe solvents were removed under reduced pressure
  10. distillationThe residue was purified by distillation (bp=180° B 185° C., 1 torr)

Sources & evidence

ORD record
ord-db1a1e831f5947948043a84a6843c17d
Source dataset
uspto-grants-2005_06
Patent number
US06906057B1

Reaction notes

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