Hexachloroethane → HCID 86726475、化合物

HRID 1487640ノート

反応式

HRID 1487640 の反応式
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[N:6]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:23]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[Cl:23][C:9]1[N:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]=[CH:7][C:8]=1[N+:10]([O-:12])=[O:11]

参加物

6

反応物 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 578205541-(2-Methoxyethyl)-4-nitro-1H-pyrazole

生成物 1

HCID 86726475HCID 86726475、化合物収率 83%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1-(2-methoxyethyl)-4-nitro-1H-pyrazole (1 equiv) in THF (0.5 M) was added dropwise lithium bis(trimethylsilyl)amide (2.7 equiv) in THF (1.0 M) at −78° C. The reaction was stirred at −78° C. for 30 min before the addition of hexachloroethane (1.5 equiv) in THF (1.84 M). The reaction was stirred at −78° C. for 2.5 h before warming to room temperature. The reaction was diluted with brine and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (10-20% ethyl acetate in petroleum ether) to afford the desired product as a yellow solid (83% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.13 (s, 1H), 8.08 (s, 1H), 4.31-4.28 (t, J=4.2 Hz, 2H), 3.74-3.72 (t, J=5.36 Hz, 2H), 3.37 (s, 3H).

後処理

  1. temperaturebefore warming to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (10-20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-cc30a75218794d8381c71416b9686241
出典データセット
uspto-grants-2016_08
特許番号
US09428509B2

反応ノート

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