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

HRID 490403Notes

Reaction equation

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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-8880710263c544cc8a72a97a72f433ef
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528157B2

Reaction notes

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