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

HRID 605487ノート

反応式

HRID 605487 の反応式
[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]

参加物

4

反応物 2

HCID 8472Trimethyl phosphite2 回HCID 57429591HCID 57429591、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fa938ac63f194b4ab2996dd16f99f14c
出典データセット
uspto-grants-2011_03
特許番号
US07915242B2

反応ノート

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