Trimethylsilylacetylene → 2-Methyl-4-trimethylsilanylethynyl-1-trimethlsilanyloxymethyl-benzene

HRID 51796ノート

反応式

HRID 51796 の反応式
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][O:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>C(N(CC)CC)C.[Cu]I.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>[CH3:14][C:4]1[CH:3]=[C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:13]=[CH:12][C:5]=1[CH2:6][O:7][Si:8]([CH3:11])([CH3:10])[CH3:9]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 22568853(4-Bromo-2-methyl-benzyloxy)-trimethylsilane2 回

生成物 1

HCID 225688632-Methyl-4-trimethylsilanylethynyl-1-trimethlsilanyloxymethyl-benzene収率 65.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

Using General Procedure D; (4-bromo-2-methyl-benzyloxy)-trimethylsilane (Intermediate 134, 550.0 mg, 2.01 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (38.0 mg, 0.20 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (1.05 g, 10.6 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (142.0 mg, 0.20 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (380.0 mg, 65%) was isolated by chromatography (0-2% EtOAc-hexanes) as an orange oil.

後処理

  1. customsparged with argon for 5 minutes
  2. customThe resulting reaction mixture

出典と根拠

ORDレコード
ord-028ed70db1714b838868c3b3f58cbb84
出典データセット
uspto-grants-2004_03
特許番号
US06713647B2

反応ノート

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