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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 24069Generated: October 30, 2026

Dichloromethane → 2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic Acid

https://huagongshe.com/reaction/24069

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantCyclopropylamineHCID 69828—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl esterHCID 12971712—
SolventAcetic AcidHCID 176—
SolventAcetonitrileHCID 6342—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
Product2-Fluoro-4-(8,8-dimethl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2yl-ethynyl)-benzoic AcidHCID 9967569—

Reaction Steps

Following general procedure G and using 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester (Compound 9, 0.132 g, 0.3 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.18 g, 2.86 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.1 g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06855512B2
Source datasetuspto-grants-2005_02
ORD IDord-90ad7be99a7242a3bf87b1342fa344e4
Source noteuspto-grants-2005_02