Pyridine → 3-Bromo-1-(triisopropylsilyl)pyrrole

HRID 389004

反応式

HRID 389004 の反応式
C1C(=O)N([Br:8])C(=O)C1.[CH:9]([Si:12]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1)([CH3:11])[CH3:10].N1C=CC=CC=1.CCCCCC>C1COCC1>[Br:8][C:15]1[CH:16]=[CH:17][N:13]([Si:12]([CH:9]([CH3:11])[CH3:10])([CH:18]([CH3:20])[CH3:19])[CH:21]([CH3:23])[CH3:22])[CH:14]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 8058HexaneHCID 67184N-bromobutanimideHCID 145136N-Triisopropylsilylpyrrole

生成物 1

HCID 27633023-Bromo-1-(triisopropylsilyl)pyrrole収率 90.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NBS (N-bromosuccinimide; 0.8 g, 4.5 mmol) was added to a stirred solution of N-(triisopropylsilyl)pyrrole (1.0 g, 4.5 mmol) in anhydrous THF (10 mL) at −78° C. The reaction mixture was kept at −78° C. for 1-2 h and then left to reach room temperature (ca. 1 h). Pyridine (0.1 mL) and hexane (10 mL) were added, the resulting suspension was filtered through a plug of neutral alumina, and the filtrate was evaporated in vacuum. Purification by column chromatography on silica gel (hexane/ethyl acetate=10:1) gave oil (1.22 g, 90.1% yield). 1H NMR (CDCl3) δ 6 1.08 (d, 18 H, Hz, Me), 1.42 (sept, 3 H, CH), 6.26 (dd, 1H, H-4), 6.66 (t, 1 H, H-5), 6.72 (dd, 1H, H-2). MS (M+H) m/z 302.

後処理

  1. waitleft
  2. customto reach room temperature
  3. custom(ca. 1 h)
  4. filtrationthe resulting suspension was filtered through a plug of neutral alumina
  5. customthe filtrate was evaporated in vacuum
  6. customPurification by column chromatography on silica gel (hexane/ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-06fa717293be470eba1aa01f85853a1e
出典データセット
uspto-grants-2013_02
特許番号
US08378058B2

関連ノート

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