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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1596870Generated: October 31, 2026

Dichloromethane → [2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl-ethynyl)phenyl]-acetic Acid

https://huagongshe.com/reaction/1596870

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantCyclopropylamineHCID 69828—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant[2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl esterHCID 69548870—
SolventAcetic AcidHCID 176—
SolventAcetonitrileHCID 6342—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
Product[2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl-ethynyl)phenyl]-acetic AcidHCID 9968269—

Reaction Steps

Following general procedure G and using [2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester (Compound 14, 0.258 g, 0.68 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.266 g, 4.23 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20-25% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.21 g, 73%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06291677B1
Source datasetuspto-grants-2001_09
ORD IDord-518f5d38926e4975a466f1e91a22a798
Source noteuspto-grants-2001_09