Propionic Acid → (E)-5-(4-ethoxycarbonyl-2-methylbut-1-enyl)furan-2-carboxylic acid benzyl ester

HRID 332611Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([CH:16](O)[C:17]([CH3:19])=[CH2:18])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](OCC)([O:25][CH2:26][CH3:27])[O:22]CC.[C:31](O)(=O)CC>>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13](/[CH:16]=[C:17](\[CH3:19])/[CH2:18][CH2:31][C:21]([O:25][CH2:26][CH3:27])=[O:22])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 31214Ethyl orthoformate

HCID 866733225-(1-Hydroxy-2-methylprop-2-enyl)furan-2-carboxylic acid benzyl ester

Product 1

HCID 70869498(E)-5-(4-ethoxycarbonyl-2-methylbut-1-enyl)furan-2-carboxylic acid benzyl esterYield 161.1%

Conditions

Temperature: 138 °C

Procedure

To the compound (332 mg, 1.23 mmol) obtained in step 1 were added triethyl orthoformate (5.0 mL, 27 mmol) and propionic acid (0.020 mL, 0.27 mmol), and the mixture was stirred at 138° C. overnight. The reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=90/10) to give the title compound (149 mg, 0.435 mmol, 35%).

Workup

customThe reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=90/10)

Sources & evidence

ORD record: ord-9c54df00d4754eee81e29c89d4021385
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877805B2

Reaction notes

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