Hexane → HCID 18673776、化合物

HRID 2299034ノート

反応式

HRID 2299034 の反応式
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[N:14]=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>CCOCC>[CH2:20]([O:19][C:15]1[N:14]=[C:13]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])[CH:18]=[CH:17][CH:16]=1)[CH3:21]

参加物

6

反応物 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 12010182-Bromo-6-ethoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 18673776HCID 18673776、化合物収率 34.4%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A 2.5M solution of n-butyllithium in hexane (4.5 ml, 11.3 mmol) was added to a stirred solution of 2-bromo-6-ethoxypyridine (Rec. Trav. chim., 1965, 84, 53; 2.1 g, 11.3 mmol) in anhydrous ether (25 ml), under nitrogen, at about −40° C. After about 20 minutes, tri-n-butyltin chloride (3.1 ml, 11.4 mmol) was slowly added and, after a further 15 minutes, the reaction mixture was allowed to warm to room temperature. The resulting mixture was quenched by the addition of aqueous ammonium chloride solution, then the organic phase separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography, using an elution gradient of pentane:dichloromethane (100:0 to 80:20), to give the title compound (1.6 g, 34%) as a colourless oil. δ(CDCl3): 0.90 (t,9H), 1.08 (t,6H), 1.30-1.42 (m,9H), 1.58 (m,6H), 4.40 (q,2H), 6.53 (d,1H), 6.97 (d,1H), 7.39 (dd,1H).

後処理

  1. customThe resulting mixture was quenched by the addition of aqueous ammonium chloride solution
  2. customthe organic phase separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-10064a0595f443ea92d1f483a742133a
出典データセット
uspto-grants-2002_12
特許番号
US06495568B1

反応ノート

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