Trimethylsilylacetylene → Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

HRID 1473023

反応式

HRID 1473023 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>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>[CH3:13][Si:14]([C:17]#[C:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10])([CH3:16])[CH3:15]

参加物

4

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 640185Methyl 2-(2-iodophenyl)acetate

生成物 1

HCID 59457733Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

実験手順

Methyl 2-(2-iodophenyl)acetate (I9) (4.65 g, 16.8 mmol), PdCl2(PPh3)2 (295 mg, 421 μmol) and Cu(I)I (80.0 mg, 421 μmol) were placed into an oven dried reaction flask under nitrogen. (Trimethylsilyl)acetylene (2.80 mL, 20.2 mmol), dry degassed THF (20 mL) and triethylamine (20 mL) were added and the reaction mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure to give a black residue which was adsorbed onto silica then chromatographed on silica gel (0-5% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I10) (4.63 g, 99%) as a light brown liquid; 1H NMR (400 MHz, CDCl3) δ 7.48 (dd, J=7.5, 0.8 Hz, 1H), 7.32-7.14 (m, 3H), 3.84 (s, 2H), 3.71 (s, 3H), 0.26 (s, 9H). LCMS Method C: rt 6.64 min.

後処理

  1. customdried
  2. customreaction flask under nitrogen
  3. customdegassed THF (20 mL) and triethylamine (20 mL)
  4. additionwere added
  5. customThe volatiles were removed under reduced pressure
  6. customto give a black residue which
  7. customthen chromatographed on silica gel (0-5% ethyl acetate/petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-2dcc2fc004c045128958145b2b8d6029
出典データセット
uspto-grants-2015_04
特許番号
US09012461B2

関連ノート

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