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

HRID 2266853Notes

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-62f985a08ab44c5c826d4f0033738e02
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858644B2

Reaction notes

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