4-Toluenesulfonyl chloride → Methyl 4-(chloromethyl)-5-methylfuran-2-carboxylate

HRID 490403ノート

反応式

HRID 490403 の反応式
C(N(CC)CC)C.CC1C=CC(S([Cl:18])(=O)=O)=CC=1.[CH3:19][O:20][C:21]([C:23]1[O:24][C:25]([CH3:30])=[C:26]([CH2:28]O)[CH:27]=1)=[O:22]>ClCCl>[CH3:19][O:20][C:21]([C:23]1[O:24][C:25]([CH3:30])=[C:26]([CH2:28][Cl:18])[CH:27]=1)=[O:22]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58824163Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate

生成物 1

HCID 914782Methyl 4-(chloromethyl)-5-methylfuran-2-carboxylate収率 33.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Triethylamine (196 μl, 1.41 mmoles), followed by 4-methyl-benzenesulphonyl chloride (247 mg, 1.293 mmoles) were added to a stirred solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (200 mg, 1.176 mmoles) in dry dichloromethane at 0° C. under an argon atmosphere. The reaction mixture was stirred at 0° C. for 15 minutes, then allowed to warm to room temperature and was stirred for a further 4 hours. The mixture was washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), and dried (MgSO4). After removal of the solvent, the residue was purified by flash chromatography, using petrol/diethyl ether 19:1 v/v as eluent, to afford compound 159 (75 mg) as a white solid. LC/MS System D; Rt=6.34 mins, m/z (ES+)=189 (M+H for C8H9ClO3).

後処理

  1. temperatureto warm to room temperature
  2. stirringwas stirred for a further 4 hours
  3. washThe mixture was washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent
  6. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-8880710263c544cc8a72a97a72f433ef
出典データセット
uspto-grants-2009_05
特許番号
US07528157B2

反応ノート

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