Tetrabutylammonium Fluoride → Methyl 2-(2-ethynylphenyl)acetate

HRID 1473024

反応式

HRID 1473024 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])#[CH:5]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 59457733Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

生成物 1

HCID 45789861Methyl 2-(2-ethynylphenyl)acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate (I10) (4.63 g, 19.0 mmol) was dissolved in DCM (200 mL) and TBAF (1.0 M in THF) (28.5 mL, 28.5 mmol, 1.5 eq) was added at 0° C. The resulting solution was stirred at room temperature for 1 hour before washing with 10% NaHCO3 (100 mL). The organic layer was dried (MgSO4) then evaporated under reduced pressure to give a dark brown/black residue. The residue was adsorbed onto silica and then chromatographed on silica gel (0-10% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I4) (2.76 g, 83%) as a red liquid; 1H NMR (400 MHz, CDCl3) δ 7.52 (dd, J=7.6, 1.1 Hz, 1H), 7.43-7.16 (m, 3H), 3.88 (d, J=9.6 Hz, 2H), 3.77-3.52 (m, 3H), 3.28 (s, 1H).

後処理

  1. washbefore washing with 10% NaHCO3 (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthen evaporated under reduced pressure
  4. customto give a dark brown/black residue
  5. customchromatographed on silica gel (0-10% ethyl acetate/petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-55180e6b4720488992bba2a427f60ef7
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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