Water → 4-Isopropyl-2-(tributylstannyl)thiazole

HRID 925946ノート

反応式

HRID 925946 の反応式
[CH:1]([C:4]1[N:5]=[CH:6][S:7][CH:8]=1)([CH3:3])[CH3:2].[Li]CCCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].O>C1COCC1>[CH:1]([C:4]1[N:5]=[C:6]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])[S:7][CH:8]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 200843694-IsopropylthiazoleHCID 178418339Butyllithium

生成物 1

HCID 575787544-Isopropyl-2-(tributylstannyl)thiazole収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of 4-isopropylthiazole (9 g, 71 mmol) in anhydrous THF (100 mL) at −78° C. was added nBuLi (40 mL, 99 mmol). The reaction was stirred for 1 hr and the temperature reached −40° C. The reaction mixture was cooled to −78° C. and tri-n-butyltinchloride (23 g, 71 mmol) was added. The reaction mixture was stirred at room temperature for 48 hrs. Water was added and solvent was evaporated under reduced pressure. The residue was partioned between water and EtOAc. Organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 219 as colorless oil in 55% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 0.88-1.62 (m, 27H), 1.40 (s, 3H), 1.42 (s, 3H), 3.17-3.24 (m, 1H).

後処理

  1. customreached −40° C
  2. stirringThe reaction mixture was stirred at room temperature for 48 hrs
  3. customsolvent was evaporated under reduced pressure
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-031d12fa24294639b839f8f1e5449b36
出典データセット
uspto-grants-2016_03
特許番号
US09284307B2

反応ノート

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