Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1907747Generated: October 31, 2026

Methanol → (2E,4E)-4-(1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoic acid

https://huagongshe.com/reaction/1907747

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantLithium HydroxideHCID 3939—
ReactantTetrahydrofuranHCID 8028—
Reactant(2E,4E)-Ethyl 4-(1-(benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoateHCID 59737265—
SolventWaterHCID 962—
Product(2E,4E)-4-(1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoic acidHCID 59737348—

Reaction Conditions

Temperature-78 °C

Reaction Steps

A solution of ester 275 (0.15 g, 0.485 mmol) in 2:1 THF:MeOH (6 mL) was treated with a solution of lithium hydroxide (59 mg, 1.41 mmol) in H2O (3 mL) and stirred for 18 h. The reaction mixture was quenched with 1N HCl (2.0 mL), concentrated, diluted with H2O, cooled to −78° C. and lyophilized to provide title compound 276 (quantitative, in a mixture with LiCl).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598168B2
Source datasetuspto-grants-2013_12
ORD IDord-92d5f264282744acb69bd5daad313487
Source noteuspto-grants-2013_12