Ethyl Acetate → 6-(Benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoic acid

HRID 2177681Notes

Reaction equation

O.[OH-].[Li+].[C:4]1([S:10]([CH2:13][C:14]2[C:19]([C:20]([O:22]C)=[O:21])=[C:18]([CH2:24][CH3:25])[C:17]([C:26]3[CH:30]=[CH:29][O:28][CH:27]=3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O1CCOCC1.O>[C:4]1([S:10]([CH2:13][C:14]2[C:19]([C:20]([OH:22])=[O:21])=[C:18]([CH2:24][CH3:25])[C:17]([C:26]3[CH:30]=[CH:29][O:28][CH:27]=3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Lithium hydroxide monohydrate (0.075 g) was added to a solution of methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate (Intermediate 152, 0.092 g) in dioxane (1 ml) and water (1 ml) and the resultant solution was stirred and heated in the microwave at 150° C. for 4.5 hours. Ethyl acetate and water were added and the organic layer was separated, then acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl aceate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness then azeotroped with toluene. The residue was triturated with ether and the solid was collected by filtration and dried to give 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoic acid (0.027 g) as a white solid.

Workup

customthe organic layer was separated
extractionThe mixture was extracted with ethyl aceate
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthen azeotroped with toluene
customThe residue was triturated with ether
filtrationthe solid was collected by filtration
customdried

Sources & evidence

ORD record: ord-c5499c1ca6e54861a797e496ee6a37df
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

Loading…