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

HRID 928123노트

반응식

HRID 928123 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-bef95277b735410194c9b8f242854e50
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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