Methyl 5-formyl-2-methylfuran-3-carboxylate → 5-(1-Hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester

HRID 68573

Reaction equation

[CH3:1][Mg]Br.[CH3:4][O:5][C:6]([C:8]1[CH:12]=[C:11]([CH:13]=[O:14])[O:10][C:9]=1[CH3:15])=[O:7]>C1COCC1>[CH3:4][O:5][C:6]([C:8]1[CH:12]=[C:11]([CH:13]([OH:14])[CH3:1])[O:10][C:9]=1[CH3:15])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Methylmagnesium bromide (370.5 ml, 1.4M in THF) is added over 30 minutes to a solution of 5-formyl-2-methyl-furan-3-carboxylic acid methyl ester (87.2 g) in THF (1200 ml) under nitrogen at 0° C. After 1 hour at 0° C., the reaction is quenched with a saturated aqueous solution of NH4Cl in water. The mixture is stirred 1 hour at 0° C. and then is extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in verve to yield 5-(1-hydroxy-ethyl)-2-methyl-furan-3-carboxylic acid methyl ester (94.5 g) as a yellow solid. The crude product obtained is used without further purification. MS (HPLC/MS): 185 (MH+).

Workup

customthe reaction is quenched with a saturated aqueous solution of NH4Cl in water
extractionis extracted three times with ethyl acetate
dry with materialdried over Na2SO4
concentrationconcentrated in verve

Sources & evidence

ORD record: ord-b77cf627339442168587cf1cd4d38791
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822466B2

Linked notes

Loading…