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3-Oxotetrahydrofuran → HCID 89923682、化合物

HRID 626984
ノート
印刷プレビュー

反応式

HRID 626984 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.C([Li])CCC.[O:14]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]1>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:16]2([OH:19])[CH2:17][CH2:18][O:14][CH2:15]2)=[N:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5293923-OxotetrahydrofuranHCID 70066515-Bromo-2-iodopyrimidineHCID 178418339Butyllithium

生成物 1

HCID 89923682HCID 89923682、化合物収率 25%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

5-Bromo-2-iodopyrimidine (10 g, 35.1 mmol) was dissolved in dry toluene (100 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 14.7 mL) was added dropwise and the reaction mixture was aged for 30 minutes prior to dropwise addition of oxolan-3-one (2.97 mL, 38.6 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature for 1 h. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed successively with water and brine, then dried over magnesium sulphate. The solvent was removed under reduced pressure to afford a dark yellow oil. The crude material was purified by chromatography on silica (Biotage, 100 g cartridge), eluting with 0-100% ethyl acetate in heptanes, to afford the title compound (2.15 g, 25% at 86% purity) as a yellow oil. δH (500 MHz, DMSO-d6) 9.01 (s, 2H), 5.66 (s, 1H), 3.99-3.93 (m, 2H), 3.88-3.77 (m, 2H), 2.46 (dt, J 12.6, 8.9 Hz, 1H), 2.16 (ddd, J 12.6, 6.4, 3.5 Hz, 1H).

後処理

  1. temperatureto warm to room temperature for 1 h
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed under reduced pressure
  6. customto afford a dark yellow oil
  7. customThe crude material was purified by chromatography on silica (Biotage, 100 g cartridge)
  8. washeluting with 0-100% ethyl acetate in heptanes

出典と根拠

ORDレコード
ord-7d4e0315e0ab45b2837799ef39f27430
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309243B2

反応ノート

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