Water → Methyl 5-(3-oxopropyl)furan-2-carboxylate

HRID 491403Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])O.[Na+].[CH2:16]([OH:19])[CH:17]=[CH2:18].O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH:16]([CH2:17][CH2:18][C:7]1[O:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][CH:8]=1)=[O:19]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 5-bromo-2-furancarboxylic acid methyl ester (816 mg, MAYB) in DMF (3 ml) was added with tetra-n-butylammonium chloride (1.1 g, TCI), sodium hydrogencarbonate (688 mg), palladium acetate (10.4 mg, WAKO), and allyl alcohol (346 mg, TCI), and the mixture was stirred at 60° C. for 20 hours. The reaction solution was added with distilled water (30 ml), and ethyl acetate (20 ml), and the insoluble solid was removed by filtration. The filtrate was extracted with ethyl acetate (50 ml×2). The organic layers were combined, washed with saturated brine, and dried, and then the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Flash, hexane:ethyl acetate=4:1) to obtain the title compound (Intermediate ih-01, 204 mg).

Workup

customthe insoluble solid was removed by filtration
extractionThe filtrate was extracted with ethyl acetate (50 ml×2)
washwashed with saturated brine
customdried
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography (Flash, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-9400ccdb69da490ba630e83494046cda
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531533B2

Reaction notes

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