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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61864Generated: October 27, 2026

Toluene → HCID 178504566, compound

https://huagongshe.com/reaction/61864

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantTriphenylphosphineHCID 11776—
ReactantDiethyl azodicarboxylateHCID 5462977—
Reactant(4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-olHCID 66834506—
Reactant2,3-Dichloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 66834562—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178504566HCID 17850456667%

Reaction Conditions

Temperature40 °C

Reaction Steps

Under nitrogen atmosphere, to the THF (0.3 mL) solution of 2,3-dichloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound Y4, 12.9 mg, 0.0373 mmol), (4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ol (15.5 mg, 0.0559 mmol) and triphenylphosphine (14.7 mg, 0.0559 mmol), toluene solution (25.4 μL, 0.0559 mmol) of DEAD was added dropwise at room temperature. The reaction mixture was stirred at ambient temperature of 40° C. for 4 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by preparative TLC (Merck 60 F254, 0.5 mm) {solution for elution:hexane/ethyl acetate (3:1)} to obtain the title compound (white solid, 15.1 mg, 67%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440922B2
Source datasetuspto-grants-2016_09
ORD IDord-c076607dd855488094b4e339807f6902
Source noteuspto-grants-2016_09