Trimethylsilyl iodide → HCID 76684539、化合物

HRID 925219ノート

反応式

HRID 925219 の反応式
C(OC([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12]([CH3:21])([CH3:20])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=O)C.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[F:19][C:13]1([F:18])[C:12]([CH3:20])([CH3:21])[C:11]2[C:10]3[CH2:22][CH2:23][NH:6][CH2:7][CH2:8][C:9]=3[CH:17]=[CH:16][C:15]=2[CH2:14]1

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 86725332HCID 86725332、化合物

生成物 1

HCID 76684539HCID 76684539、化合物収率 30.7%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

Into a glass vial containing the product from step (c) (20 mg, 0.061 mmol) dissolved in CHCl3 (2 ml), TMSI (84 μL, 0.619 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours. The volatiles were evaporated in vacuo and the residue diluted with 2M HCl (2 ml) and water (20 ml). The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the title compound as a colorless oil (4.7 mg). 1H NMR (300 MHz, CDCl3) δ 6.99-6.96 (m, 2H); 3.28 (t, J=14.1 Hz, 2H); 3.03-2.90 (m, 8H); 1.89 (bs, 1H); 1.39 (s, 6H); MS: ESI (positive): 252 (M+1).

後処理

  1. customThe volatiles were evaporated in vacuo
  2. additionthe residue diluted with 2M HCl (2 ml) and water (20 ml)
  3. washThe aqueous mixture was washed with diethyl ether (2×)
  4. extractionextracted with DCM (3×)
  5. washThe combined DCM extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-eeb9c80507bb4451995fb002fb13d26d
出典データセット
uspto-grants-2016_03
特許番号
US09284277B2

反応ノート

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