Water → 5-[(Trimethylsilyl)ethynyl]thiophen-2-ylmethyl Tert-butyldiphenylsilyl Ether

HRID 1281232ノート

反応式

HRID 1281232 の反応式
[Si:1]([O:18][CH2:19][C:20]1[S:21][C:22](Br)=[CH:23][CH:24]=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.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].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[S:21][C:22]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:23][CH:24]=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

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 22393098(5-Bromothiophen-2-yl)methyl Tert-butyldiphenylsilyl Ether2 回

生成物 1

HCID 223930945-[(Trimethylsilyl)ethynyl]thiophen-2-ylmethyl Tert-butyldiphenylsilyl Ether

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 3283Diethyl Ether溶媒

実験手順

A 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 2.16 g (5.0 mmol) of (5-bromothiophen-2-yl)methyl tert-butyldiphenylsilyl ether (Compound 12), 2.12 mL (15 mmol) of (trimethylsilyl)acetylene, and 17.5 mL of triethylamine. The solution was purged with argon for 15 min and bis(triphenylphosphine)palladium (II) chloride (88 mg, 0.125 mmol) and copper (I) iodide (24 mg, 0.125 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 silica gel chromatography (hexane) to give the title compound.

後処理

  1. customA 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 min
  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. customThe residue was purified by silica gel chromatography (hexane)

出典と根拠

ORDレコード
ord-ce572aa551f84ff9924e0e2a379233f9
出典データセット
uspto-grants-2002_09
特許番号
US06452032B1

反応ノート

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