2-Propynoic acid, 3-phenyl-, ethyl ester → Ethyl-4-phenyl-3-furoate

HRID 915670

Reaction equation

HRID 915670 reaction equation
[C:1]1([C:7]2N=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])C=CC=CC=1>C(OCC)(=O)C>[CH2:23]([O:22][C:20]([C:19]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][O:10][CH:9]=1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 915162-Propynoic acid, 3-phenyl-, ethyl esterHCID 5892794-Phenyl-1,3-oxazole

Product 1

HCID 15037153Ethyl-4-phenyl-3-furoateYield 78.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
220 °C

Procedure

Mix 4-Phenyl oxazole (3.33 g, 23.0 mmol) and ethyl phenylpropiolate (4.0 g, 23.0 mmol) in a sealed tube and heat at 220° C. for 20 hours. Perform flash-chromatography on silica gel eluting with 4:1 Hex/ethyl acetate to afford 3.9 g of 4-phenylfuran-3-carboxylic acid ethyl ester as a yellow oil. MS: m/e=217 (MH+).

Sources & evidence

ORD record
ord-9fd118029536481387b3a1242356d996
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Linked notes

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