Ammonium Chloride → ({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

HRID 2184352ノート

反応式

HRID 2184352 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C.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>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:9][CH:8]=1

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

生成物 1

HCID 22476627({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

A well stirred suspension of 4.0 g (12.2 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 0.23 g (1.22 mmol) of cuprous iodide and 0.856 mg (1.22 mmol) of dichloro bis(triphenylphosphine) palladium(II) in a mixture of 20 ml THF and 10 ml triethylamine is treated dropwise with 1.44 g (14.6 mmol) of trimethylsilyl acetylene. The reaction is exothermic. The mixture is stirred overnight at RT, treated with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The organic phase is dried, concentrated and subjected to flash-chromatography (silica gel, cyclohexane) to yield 3.48 g (95%) of a slightly orange oil. NMR (CDCl3; 300 MHz): 0.24 ppm (s, 9H); 5.06 ppm (s, 2H); 6.85-7.45 ppm (m, 8H).

後処理

  1. stirringThe mixture is stirred overnight at RT
  2. extractionextracted three times with ethyl acetate
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customto yield 3.48 g (95%) of a slightly orange oil

出典と根拠

ORDレコード
ord-4e7f55ff111443c98ea684cd3c74b685
出典データセット
uspto-grants-2005_05
特許番号
US06900354B2

反応ノート

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