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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2214296Generated: October 30, 2026

Ethyl Acetate → 5-Methyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromene-2,8-diol

https://huagongshe.com/reaction/2214296

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantAmmonium ChlorideHCID 25517—
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant1-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-pyrrolidineHCID 21959284—
SolventTetrahydrofuranHCID 8028—
Product5-Methyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,11-dihydro-chromeno[4,3-c]chromene-2,8-diolHCID 21959145—

Reaction Steps

To a solution of 1-(2-{4-[2,8-bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-pyrrolidine (84.5 mg, 0.12 mmol) in THF (7 mL) was added tetrabutylammonium fluoride (1M in THF, 241.4 μL, 0.24 mmol). The mixture was stirred at room temperature for 40 min. Saturated NH4Cl was added followed by addition of ethyl acetate. The resulting layers were separated, the organic layer was washed with brine, and dried over MgSO4. The solvent was evaporated and the residue dried under vacuum for 2 h at room temperature to yield the title compound which was carried on to the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07105679B2
Source datasetuspto-grants-2006_09
ORD IDord-59ebf7e8cfb041c08b4f3e0e357c4140
Source noteuspto-grants-2006_09