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

HRID 460101노트

반응식

HRID 460101 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-af62dbe1d1cb4a00a451868157447a4a
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196089B2

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