Sodium Thiosulfate Pentahydrate → Methyl 4-formyl-5-methylfuran-2-carboxylate

HRID 490401Notes

Reaction equation

C(OI1(OC(=O)C)(OC(=O)C)C2C(=CC=CC=2)C(=O)O1)(=O)C.[CH3:23][O:24][C:25]([C:27]1[O:28][C:29]([CH3:34])=[C:30]([CH2:32][OH:33])[CH:31]=1)=[O:26].C(=O)(O)[O-].[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(OCC)C>[CH3:23][O:24][C:25]([C:27]1[O:28][C:29]([CH3:34])=[C:30]([CH:32]=[O:33])[CH:31]=1)=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Acetic acid 1,1-diacetoxy-3-oxo-1λ5-ioda-2-oxa-indan-1-yl ester (Dess-Martin reagent) (549 mg, 1.293 mmoles) in dry dichloromethane was added to a solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (200 mg, 1.176 mmoles) in dry dichloromethane (9 ml) with cooling to 0° C. under an argon atmosphere. After stirring for 20 minutes, the mixture was diluted with diethyl ether (40 ml) and was poured into saturated aqueous sodium bicarbonate (30 ml) containing sodium thiosulphate pentahydrate (4 g) and agitated vigorously for 5 minutes. The organic phase was washed with saturated aqueous sodium bicarbonate (40 ml), water (50 ml) and brine (50 ml) and dried. After removal of the solvent, the residue was purified by flash chromatography, using petrol/diethyl ether 4:1 v/v as eluent, to afford compound 157 (140 mg) as a white solid.

Workup

stirringagitated vigorously for 5 minutes
washThe organic phase was washed with saturated aqueous sodium bicarbonate (40 ml), water (50 ml) and brine (50 ml)
customdried
customAfter removal of the solvent
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-0fd6dcc7d9cb4cffbe29d1c7c14acfdc
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528157B2

Reaction notes

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