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

HRID 1786628Notes

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-e646003c904d4701a39f4a2a6e5f1e6f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507754B2

Reaction notes

Loading…