Triethyl phosphite → Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

HRID 928123ノート

反応式

HRID 928123 の反応式
[Br:1][C:2]1[S:6][C:5]([CH2:7]Br)=[N:4][CH:3]=1.[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([O:10][P:9]([CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

参加物

4

反応物 2

HCID 31215Triethyl phosphiteHCID 594709305-Bromo-2-(bromomethyl)-1,3-thiazole

生成物 1

HCID 86720195Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.02 g, 3.97 mmol) and triethyl phosphite (1.389 mL, 7.94 mmol) were combined in toluene (8 mL) and stirred at reflux overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate) to afford diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate as a yellow oil. MS ESI calc'd. for C8H14BrNO3PS [M+H]+ 314, 316. found 314, 316. 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 4.17-4.09 (m, 4H), 3.57 (d, J=21.2 Hz, 2H), 1.32 (t, J=7.1 Hz, 6H).

後処理

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-bef95277b735410194c9b8f242854e50
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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