Triethylamine → HCID 59536255、化合物

HRID 1181400ノート

反応式

HRID 1181400 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(N(CC)CC)C>CN(C)C=O.[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>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[C:3]=1[CH:4]=[O:5]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 224739772-Bromo-6-fluorobenzaldehyde

生成物 1

HCID 59536255HCID 59536255、化合物収率 95.6%

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 6228Dimethylformamide溶媒

実験手順

To a solution of 2-bromo-6-fluorobenzaldehyde (Description 39; 10.0 g, 49.3 mmol) and (trimethylsilyl) acetylene (13.94 ml, 98.6 mmol) in anhydrous N,N-dimethylformamide (250 ml) under an atmosphere of nitrogen was added triethylamine (10.25 ml, 73.95 mmol), copper (I) iodide (0.94 g, 4.93 mmol) and Pd(PPh3)2Cl2 (1.73 g, 2.47 mmol). The mixture was degassed and stirred at room temperature overnight. The mixture was poured into water (600 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with water (3×300 ml), brine (200 ml) then dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5% Et2O in iso-hexanes to give the title compound (10.38 g, 95%).

後処理

  1. customThe mixture was degassed
  2. additionThe mixture was poured into water (600 ml)
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. washThe combined organic layers were washed with water (3×300 ml), brine (200 ml)
  5. dry with materialthen dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel eluting with 5% Et2O in iso-hexanes

出典と根拠

ORDレコード
ord-619532a3b5ac4f41ac87106e9e6fb40a
出典データセット
uspto-grants-2007_10
特許番号
US07285563B2

反応ノート

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