4-Toluenesulfonyl chloride → 2-Nitrobenzyl tosylate

HRID 270536

反応式

HRID 270536 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl.C(N(CC)CC)C>[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:20])=[O:19]

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 119232-Nitrobenzyl alcohol

生成物 1

HCID 5616632-Nitrobenzyl tosylate収率 79%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

2-Nitrobenzyl alcohol (1 g, 6.5 mmol) was dissolved in 40 ml of dry DCM and 1.36 ml of triethylamine. p-toluenesulfonyl chloride (1.24 g, 6.5 mmol) was added and the solution was stirred for 2 hours before quenching with water. The organic layer was separated and washed with 1 N HCl (1×50 ml), water (1×50 ml), 2 N NaOH (1×50 ml), water (1×50 ml) and brine (1×50 ml). The organic layer was dried over anhydrous Na2 SO4 and concentrated under reduced pressure to give a dull white solid, which was further purified by flash chromatography (silica gel, dichloromethane/ethanol=9.5:0.5) to give 2-nitrobenzyl tosylate, 22 (1.57 g, 79%). 1H-NMR (300 MHz, CDCl3) δ 8.08-7.99 (dd, J=9.21 & 8.04 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.72-7.62 (m, 3H), 7.50 (d, J=8.85 Hz, 1H) 7.33 (d, J=8.43 Hz, 2H), 4.93 (s, 2H), 2.42 (s, 3H). 13C-NMR (60 MHz, CDCl3) δ 149.33, 146.12, 137.71, 135.27, 134.11, 133.09, 132.69, 132.57, 128.12, 123.89, 42.72, 20.64. MS (ESI): m/z 329.9 [(M+Na)]+.

後処理

  1. custombefore quenching with water
  2. customThe organic layer was separated
  3. washwashed with 1 N HCl (1×50 ml), water (1×50 ml), 2 N NaOH (1×50 ml), water (1×50 ml) and brine (1×50 ml)
  4. customThe organic layer was dried over anhydrous Na2 SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a dull white solid, which
  7. customwas further purified by flash chromatography (silica gel, dichloromethane/ethanol=9.5:0.5)

出典と根拠

ORDレコード
ord-0e8aae45c292481c9e75009d29fbe1f9
出典データセット
uspto-grants-2008_11
特許番号
US07449558B2

関連ノート

読み込み中…