Trimethyl phosphite → 1-[2-(Dimethoxy-phosphoryl)-acetyl]-cyclopropanecarboxylic acid n-butyl ester

HRID 605487노트

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HRID 605487 반응식
[CH2:1]([O:5][C:6]([C:8]1([C:11](=[O:14])[CH2:12]Br)[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:15][O:16][P:17]([O:20]C)[O:18][CH3:19]>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]([C:8]1([C:11](=[O:14])[CH2:12][P:17]([O:18][CH3:19])([O:16][CH3:15])=[O:20])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 8472Trimethyl phosphite2회HCID 57429591HCID 57429591, 화합물

생성물 1

HCID 600281941-[2-(Dimethoxy-phosphoryl)-acetyl]-cyclopropanecarboxylic acid n-butyl ester수율 59%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 16 3.42 g (13.0 mmol) and trimethylphosphite (1.95 mL, 2.05 g, 16.5 mmol) in toluene (45 mL) was refluxed for 15 hours. The solvent and remaining trimethyl phosphite were then distilled off, and the residue was purified by column chromatography (2-10% isopropanol/hexane) to give 2.26 g (7.74 mmol; 59% yield) of 17. 1H NMR (500 MHz, CDCl3) δ 0.95 (3H, t, J=7.3 Hz), 1.39 (2H, m), 1.57-1.67 (6H, m), 3.75 (2H, d, JH-P=22.1 Hz), 3.78 (6H, d, JH-P=11.1 Hz), 4.15 (2H, t, J=6.7 Hz). 13C NMR (125 MHz, CDCl3) δ 13.7, 19.2, 20.6, 30.5, 35.3, 39.8, 40.8, 52.9 (d, JC-P=6.0 Hz), 170.8, 197.0 (d, JC-P=6.3 Hz). MS (EI) m/z 292 (15, M+), 264 (17), 236 (21), 218 ((45), 191 (18), 163 (22), 150 (59), 126 (100); exact mass (ESI) calculated for C12H21O6PNa ([M+Na]+) 315.0973, found 315.0963.

후처리

  1. distillationwere then distilled off
  2. customthe residue was purified by column chromatography (2-10% isopropanol/hexane)

출처 및 근거

ORD 기록
ord-fa938ac63f194b4ab2996dd16f99f14c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915242B2

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